


Punchline

by DarcyDelaney



Category: Supernatural
Genre: Comedian!Dean, F/M, Homophobic Language, Hopeful Ending, Humor, John Winchester's A+ Parenting, Journalist!Cas, M/M, fluff with a touch of angst, mentions of physical abuse
Language: English
Status: Completed
Published: 2017-11-14
Updated: 2017-11-14
Packaged: 2019-02-02 13:29:31
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 10
Words: 34,345
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12727482
Author URL: https://archiveofourown.org/users/DarcyDelaney/pseuds/DarcyDelaney
Summary: While writing a review of an open mic night at his brother’s new comedy club, Cas Novak meets (and is immediately smitten with) up-and-coming comedian Dean Winchester. Things are going great until Dean’s dream of becoming a comedy superstar starts coming true. Cas tries to be a supportive boyfriend, but eventually, he’s faced with the challenge of figuring out what Dean loves more—comedy, or Cas himself.





	1. Chapter 1

**Author's Note:**

> y i k e s
> 
> It's finally here! I love Dean/Cas, and I love comedy, so it only made sense to try and bring those two worlds together.
> 
> SO. MANY. THANKS.  
> -To my artist, the inimitable [cardinalwrites](http://cardinalwrites.tumblr.com/), for taking on my little fic and creating art for it that made (and still makes, if I'm being honest) me want to cry with delight every time I look at it <3\. Please go check out her [art masterpost](http://cardinalwrites.tumblr.com/post/167498382244/punchline-while-writing-a-review-of-an-open-mic) and leave her all the love for her gorgeous work!  
> -To my fabulous betas (both of whom have DCBBs of their own!), [edgarallanrose](https://archiveofourown.org/works/12590400/chapters/28676316) and [justanotherbusyfangirl](https://archiveofourown.org/works/12366750/chapters/28129689), for wading through my over-punctuation and assumptions that New Yorkers would wait for crosswalk signals to change. Their wonderful DCBBs are linked to here; go check them out!
> 
> I really, really hope you enjoy reading this as much as I enjoyed writing it, and as a reminder for whenever things get rough: "Motherfuckers just wanna laugh." -Harris Wittels

When a wiry, twenty-something man shoves past Cas on the sidewalk without so much as an apology or backwards glance, Cas decides that he’s heading to the hospital.

 _His daughter was just in an accident, and the subway is delayed, as usual, so it’s faster to walk,_ he reasons with himself, adjusting his messenger bag and continuing his walk toward the A train. _Being polite is probably the last thing on his mind._

As Cas walks, he starts developing the man’s backstory, giving him a wife, a solid 9-to-5, two additional kids, a dog. It’s been a hobby of his for years, making up stories for strangers: it gives him a way to pass the time, and ultimately makes him more empathetic, makes him give a shit.

Everyone’s got a story, and one of Cas’s favorite pastimes is figuring out just what those stories are.

And if he can’t figure them out, well, then he makes them up.

Amazing everyone—including himself—Cas has managed to cobble together a career for himself telling stories, only these ones need to be fact-checked and scrutinized and 110% true.

He likes his job, sure. It’s cushy and pays well, and the fact that he can have family members ask him things like, “So, Cas, how are things at the _Times_ ?” during holidays is a nice bonus, but he’d much rather they be asking something closer to, “So, Cas, how many weeks has your book been on the _Times_ bestseller list now?”

Cas spends his free time creating worlds of his own, ones that he doesn’t need to fact-check because he’s the one making up the rules. Whatever he says, goes, no matter how outlandish, ridiculous, or just plain stupid, something he wishes more often than he’d like to admit would happen during his day job. He’s well known throughout the office for bringing to life even the dryest of stories with that skill, which is why he’s often the one assigned to them.

As Cas heads toward the subway, he realizes that’s probably the exact reason why he agreed to cover an open mic night at his older brother’s new comedy club. It’s something different, and something he could make up the rules for; it’s practically guaranteed that his brother won’t give a shit as long as it sounds good.

Gabriel had bought and revamped the Yuk-Yuk Hut, a cramped, dingy club that Cas is convinced had been breaking health and safety codes left and right, earlier that year, and was finally ready to unveil his handiwork to the world—

Or at least to a handful of people hanging out in Brooklyn on a Wednesday night.

The train isn’t crowded, but Cas opts to stand instead of grabbing a seat, wrapping his fingers around the cold metal of one of the subway’s many handrails and trying to ignore the pungent smell coming from someone in his vicinity.

Most people tend to avoid eye contact at all costs on the train, which usually makes it a prime space for people-watching, and today is no different. A few minutes into the ride, Cas notices a man who enters the train with a bright purple and pink backpack slung over one shoulder, holding the hand of a little girl who has a thin red cape tied loosely around her neck. They take a seat diagonally from him, and the girl hops up onto his lap.

 _He’s a single dad, and that’s his little girl_ , Cas starts. _She has an E-name, maybe Emily or Erin. She’s five, maybe six. Her mom, his wife, died in a car accident a few years ago, and he’s still having issues dealing with the loss. He works two jobs to be able to afford their rent and his doctor-mandated therapy sessions, which is why he’s just now picking her up from her grandmother’s house._

Cas decides that this father and daughter have had enough hardship in their lives so far, so he opts to keep the rest of their story light.

_It’s her birthday tomorrow, and her dad has been saving to get her a new bike. He’s going to surprise her with it when she gets back from school._

Almost immediately after Cas comes to that conclusion, the little girl laughs gleefully—at what, Cas can’t be sure, but it makes her dad smile, and in turn, Cas does, too. He lets his mind wander for the last few stops before his own, then gets to his feet and mentally wishes the man and his daughter a good rest of the day.

There’s a kid standing outside the subway station, tuning an acoustic guitar and humming a song melody under his breath. A few coins and dollar bills are scattered in the open, tattered guitar case at his feet.

 _This kid went to Juilliard_ , Cas thinks _, key word being_ went _. He got expelled? No, dropped out. He dropped out, but his parents don’t know yet. He’s from a well-to-do town in Connecticut, and got that guitar as a birthday present. He’s living with some friends who graduated last year in a shitty apartment in Bed-Stuy; he found a cockroach in his sneaker this morning. Busking is one of his three sources of income; he’s also a bartender, and works at a frozen yogurt shop in Times Square._

The kid finishes tuning while Cas waits to cross at the corner with a crowd of other people, and Cas winces unconsciously as he starts singing and playing guitar.

Maybe he was wrong about the whole Juilliard thing.

The crosswalk light hasn’t changed, but there’s a quick break in traffic that lasts for no more than a second, and the flood of people waiting to cross take full advantage. Cas follows the crowd across the street, pretending not to notice the middle finger the cabbie promptly points in their direction.

While Cas is walking, he pulls his phone out of his pocket and thumbs through his texts until he finds the address Gabe gave him. He does some quick mapping in his head and thinks he has a good idea of where the club is, but is interrupted by a loud, rough voice.

“Comedy tonight, headliner comedy!”

He immediately starts digging in his bag for his headphones; they won’t make any difference, he knows this guy will still try and shove a flyer at him, but they’re a comfort, and provide a small barrier between himself and the outside world. Maybe he could even pretend to be talking on the phone while walking past; that idea’s been pretty reliable before.

Cas keeps walking with his head down, pawing through his notebooks and papers until he feels his shoulder smack hard into someone in front of him.

He snaps his head up sharply and makes brief eye contact with the man, who seems unfazed, before looking back down at the sidewalk.

“Sorry,” he mumbles, still trying to find his headphones.

“Wanna see some comedy, pal? Two-for-one tonight, can’t get much better than that.”

Definitely unfazed. He sticks a neon-colored flyer down near where he knows Cas will see it, but Cas shakes his head.

“I...I’m busy tonight. Sorry,” he says, his fingers finally curling around the wires of his headphones, too late. He pulls them out and starts untangling them before hefting his messenger bag up higher on his shoulder and picking up speed.

As he walks, he can feel the man’s eyes on him, but he’s not lying, he _is_ busy, so he shoves his earbuds in his ears and resumes a podcast as he continues down the street.

Behind him, he can hear the man’s voice break through the din of pedestrians and traffic. “Best comics in all five boroughs; see ‘em before they start sellin’ out MSG!”

Somehow, Cas doesn’t think that’ll be the case.

* * *

 

The Yuk-Yuk Hut is the definition of a hole in the wall: Cas inadvertently passed it twice while trying to find the entrance.

It’s one of those clubs that’s below street level, with a small set of narrow cement stairs leading to the entrance. It’s in desperate need of a sign out front directing passersby inside, so of course, it doesn’t have one. Despite that, though, Cas can’t help but find the location appropriate. Wedged in between a pizza place and a sex shop, the club completes a perfect row of his older brother’s interests.

Cas nudges past the people hanging around in front of the surrounding shops, heads down the steps to the lower level, and pulls open the door, bracing himself as the smell of stale cigarettes and booze wafts out to greet him.

The club is more crowded than Cas had been anticipating, but he’s able to snake his way through the groups of people and secure himself a seat at a small, two-person table off to the side of the stage. It’s close enough for him to see and hear everything, but shadowed enough for him to be able to stay out of the spotlight.

He slings his bag up onto the table, effectively covering the entire surface, and barely has a chance to pull out his notepad when someone taps him on the shoulder.

“What’ll you have, sweetheart?”

He looks up to see a pretty brunette looking expectantly at him while balancing a tray already loaded with beer bottles on one hand, the other pressed firmly on her hip.

“Oh, uh, I’m fine, thanks.” Cas smiles, but she doesn’t make any move to leave. Thinking that maybe she hadn’t heard him over the bustling and chattering in the club, Cas repeats himself. “I’m all set.”

She shakes her head. “Gotta order something, hon.”

“But I don’t want anything.”

She looks at him flatly, trying to figure out if he’s trying to screw her over. “Two-drink minimum.” She nods toward a badly faded sign in the corner near the stage, and Cas squints to read it; he can just barely make out the “Two”—the rest is practically invisible.

“You’re kidding me.”

The waitress huffs out a sigh before seeming to take in Cas for the first time. In his dark jeans, nice shoes, and neatly-pressed button-up with skinny tie, he looks out of place among the other patrons in more laid back clothes, and Cas suddenly feels his cheeks redden as his self-consciousness flares. She rests her hand on his shoulder and leans down close to his ear.

“Bud Lights are two for five tonight. Cheapest you’re gonna get.”

Cas sighs and wishes Gabe had decided to warn him about this stupid minimum rule. “Please,” he mutters defeatedly. The waitress smiles and winds her way through the crowd, setting down drinks every so often with robotic efficiency. Cas pulls his notebook and pen out of his bag and flips to a clean page.

 _Two-drink minimums are_ _the worst_  
_I think I’m stepping in dried vomit. On opening night._ _  
There are way too many people here; over capacity? Fire hazard?_

Cas’ eyes dart up quickly toward the stage, which is essentially just a giant slab of wood with a black curtain draped over the brick wall behind it. A piece of printer paper with the “Yuk-Yuk Hut” scrawled across it in black Sharpie is pinned to the curtain, and Cas makes another note.

_Stage could use some love_

He writes down a few more observations and when his drinks arrive, downs the first one quicker than he’d been anticipating. While members of the crowd around him are making smalltalk with each other, Cas’ mind wanders back to the man from earlier who’d tried to sell him on a comedy show. He hadn't seen much of his face after frantically trying to avoid eye contact, but starts spinning a story for him based on the five seconds they'd interacted.

_He lives in a two-bedroom apartment with five roommates, probably above a Chinese food restaurant. Does he have a job, other than trying to sell tourists half-baked jokes and witticisms about life in the city? I doubt it._

_He didn't go to college, no student loan debt,_ Cas thinks bitterly as he remembers the $600 monthly payment to Fedloan that just cleared his account this morning. _But probably loads of credit card debt. He's not particularly good with finances._

 _There are a lot of issues in his life_ — _deadbeat parents? Distant siblings? Alcoholism? A little of all three?_ — _but somehow, he still seems confident and put-together. Women fawn over him, and even though they're less than impressed when he takes them back to his place, he still convinces them to stay._

Cas decides to stop when he realizes that instead of actually trying to let the man’s life story take him where it may, he’s just giving the guy traits that he wishes he had.

“Must be nice,” he mutters to himself, and starts doodling in the margins of his notebook.

He looks up at the sound of feedback in the mic, and sees his brother on stage, tapping it with two fingers.

“We’re _baaaaaaaaaack_ ,” he crows into the mic, to the cheers of a few audience members. Most just carry on with their conversations, and Gabe glares at them, steadily raising his voice until they get the hint. “Welcome to the grand re-opening of the Yuk-Yuk Hut,” Gabe says, spreading his arms wide. “Now with 50% less police activity due to drug busts.”

The audience laughs at Gabe’s reference to one of many things that had shut the club down in the first place, and a few folks in the back boo. Gabe squints into the light and flips them off. “Get your coke somewhere else, asshole.”

Cas makes a mental note not to go into specifics on why the club had closed in his article, then holds his pen between his teeth, his chin in his hand as he watches Gabe walk the room.

“We’re still trying to get this placed cleaned up for ya,” Gabe says, “so, uh, pardon the appearance and all that bullshit.” He glances behind him and grimaces, apparently having seen the sign for the first time; he reaches back and tears it off the curtain before crumpling it up into a ball.

Cas chuckles before taking the pen out of his mouth and crossing out his comment about the stage.

“We might still be gettin’ our sea legs here, but I can guarantee you, the comics you’re about to see are not.” He lets his teeth clack together on the “t” and grins out at the crowd, a few of whom offer half-hearted claps and whoops. “Let’s get this party started with our first comic: the one, the only, Dean Winchester.”

The audience applauds politely as Gabe hands the mic off before leaving the stage. A man, presumably Dean Winchester, flashes a quick grin and an even quicker wave at the audience before making himself comfortable.

"So," he says, leaning casually on the mic stand. "I got mugged on my way home a few nights ago. Yeah. He asked for all my money; I told him I was a comedian, and _he_ gave _me_ fifty bucks."

There's a smattering of laughter, and Dean looks down at the floor with a small grin.

"Nah, I'm sure you know that's bullshit," he continues, gesturing toward his bruised face. He loops a few inches of the cord around his wrist before starting to slowly pace the small, cramped stage.

He keeps talking—about living in New York, about how different it is from living anywhere else, about his tendency to still be mistaken for a tourist—but Cas stops focusing on his words, opting to study the comic himself instead. The stage lights are harsh and bright, so he can only take in small details at a time: the scuffed workboots that are more reminiscent of a construction worker than a comedian, the worn, faded plaid shirt that looks like it was just grabbed it out of a laundry hamper half an hour before the show, the faded jeans that have clearly seen better days. Cas' eyes eventually make their way up to Dean's face; there are dark bruises lining his jaw, as well as one under his left eye that's a deep shade of purple. His bottom lip is split and still swollen, and Cas winces unconsciously.

"Am I that ugly, pal?"

Cas is jerked out of his reverie by Dean's amused voice, and Cas’ eyes widen. Dean is looking at him, just him, and he can feel everyone else in the club staring, too.

"I, no, sorry—"

"Your face said differently." Dean does an exaggerated impression of Cas’ wince, and for the first time that night, the audience genuinely laughs. Cas’ cheeks redden furiously and he looks down, but not before he catches the quick wink Dean tosses his way.

 

 

After Dean’s set is over, Cas watches him exit stage left and head for the bar at the back of the club. Before he can talk himself out of it, Cas gets out of his chair and follows him.

Dean’s sitting on a stool with his back to him, already nursing a beer and talking with someone else, probably another comic. As Cas approaches, he suddenly realizes that he has no idea what he's planning to say to him. The other man claps Dean on the back with a grin before grabbing his own beer and heading for the stage, leaving Dean alone. Cas takes a breath, then steps forward and taps Dean on the shoulder.

When Dean turns around, Cas is struck by all the features he hadn’t been able to see as clearly from his seat in the audience. The sharp outline of his jaw, the easy smile on his face, the brightness of his green eyes, clear even in the club’s shitty lighting. It’s not a matter of _if_ Cas will make a fool out of himself in front of him; it’s more like _when_.

He’s about to say something when Dean tilts his head with a bemused smirk, green eyes narrow. “Thought you said you were busy.”

Cas falters. “I...excuse me?”

Dean shakes his head in fake solemnity and takes another drink of his beer. “Glad to see I made an impression.”

Cas stares at him, and to Dean’s credit, he stares right back. And after a few seconds, something clicks and Cas’ shoulder pulses.

“You were the one peddling comedy on the sidewalk.”

Dean barks out a laugh. “And you were the dude who blew me off.” He shakes his head again. “Shot to the heart, man.”

Cas’ eyes narrow as he studies Dean, and suddenly his original plan for conversation, as slapped together as it was, disintegrates in front of him. “I’m here, aren’t I?”

Dean raises his eyebrows and purses his lips, which are shining with traces of the beer he’d been drinking. Cas licks his own unconsciously. “Damn, I’m good.”

Cas rolls his eyes. “I may be here, but I can assure you, it’s not because of your encouragement.”

Dean chuckles. “Keep tellin’ yourself that, pal.” He pats the worn vinyl seat next to him and tips his head back to take another drink.

Cas hesitates, but eventually edges onto the barstool, awkwardly balancing the soles of his feet on the steel footrest attached near the bottom. “Do you remember all the people who blow you off on the street?”

“Only the cute ones,” Dean says, and there’s that goddamn _wink_ again. “So,” he continues, setting his bottle down on the bar, “if it wasn’t me who got you to show up here, what was it? Because, and no offense, man, but you don’t really seem like you spend a lot of time outside of John Varvatos.”

Cas raises his eyebrows, then glances down to his outfit, which has betrayed him for the second time tonight. “My brother owns the place, and asked me to cover tonight for some more exposure.”

“Shit, you’re Gabe’s brother?” Dean asks. His eyes dart toward the stage, where Gabe is sweet-talking two women in the front row, then back to Cas.

Cas nods. “Shocking, I know.” He pauses for a second, then decides to steer his original conversation back on track. “I’m also the, uh, the ‘cringe guy,’ and I—”

Dean chuckles. “Shit, didn’t mean to call you out back there, man. People in the front rows are always pretty easy targets for crowd work.” He shrugs and smiles apologetically.

Cas waves it away. “Thank you, but I just, I don’t know, wanted to make sure you were all right, I suppose.”

“‘M fine,” he says, setting his empty bottle down on the bar again and rubbing at the back of his neck, his eyes trained on the club floor. “It’s the city. Sucks, but shit like that happens sometimes. Could’ve been worse.”

Cas nods sympathetically and Dean grins almost sheepishly, glancing down at his boots. He looks up again, almost like he’s about to try and keep the conversation going, but before he can, Gabe’s voice crackles through the club and interrupts them.

“Our next comic, Benny Lafitte, folks!” Cas turns toward the stage to see the man who had been talking with Dean earlier amble up to the stage. He takes the mic from Gabe and shakes his hand before launching into his own routine, starting with a little crowd banter.

“Thanks, Gabe. Hey, guys, give it up for my pal Dean again, huh? Wasn’t he great?” The applause from the crowd swells, but it’s clearly done out of obligation, and Cas notices Dean smirk and hold his hand high, flipping Benny off. Benny returns the gesture with a pair of puckered lips and a loud kissing sound before starting to talk about his encounter with a group of tourists in Washington Square Park earlier that week.

Cas turns back to Dean and jerks his thumb toward the stage. “Friend of yours?”

“Yeah. We were in the same improv class. Way back before we realized we’re both shit at it, and found standup instead.”

The idea of going up on stage with a prepared routine is terrifying enough, and the idea of the exact opposite almost makes Cas’ blood run cold. “I’d be awful at that kind of thing,” he says, offering the understatement of the century.

“It’s not that hard,” Dean says. “It’s a lot of fun, once you get over the whole ‘fear of making yourself look like a giant asshole’ part.” He nudges Cas’ shoulder gently with his own. “Bet you’d be good at it.”

“I appreciate the vote of confidence,” Cas says, trying to act more composed than he’s actually feeling. His shoulder is on fire from the slight warmth of Dean’s touch, and the other man chuckles, eyes sparkling with a mix of booze and endearment, and Cas is sure he’s about to say something else when Gabe appears out of nowhere and claps Dean on the back, almost making him spill his beer.

“Heya, Dean-o! Great set, kid,” he says. Dean takes a second to right himself and wipes his mouth with the back of his hand before turning his barstool around to face the emcee. “Those ladies over at table three really enjoyed your set; why don’t you go over and say hi, make some smalltalk?”

Dean pauses, looks from Cas to Gabe and then back to Cas. “Gabe, I—”

“Just a few minutes, dude, work with me here,” he mutters, grabbing Dean’s wrist and pulling him toward a table full of thirty-something women drinking colorful martinis and splitting three different plates of reheated appetizers. They’ve got to be the ones pulling in most of the money for the night, so Cas can immediately understand why his brother wants to keep them happy—sending a gorgeous, funny man their way is definitely an effective way to do it.

Dean glances back over his shoulder at Cas. “Sorry,” he says, “but hey, it was nice to meet you…”

“Cas.”

“Cas,” Dean repeats, nodding. “Thanks for making sure I was okay.” He flashes one more warm smile before Gabe leads him over to table three.

Cas’ eyes follow Dean as he heads toward the table, and he forces down the urge to scramble over and join them, just to have a chance to talk to him some more. Instead, he stays awkwardly perched on the barstool, watching the latest comedian—Benny—without taking in a word he’s saying.

“Hey.”

Cas turns around quickly when he feels a tap on the shoulder, half-expecting Dean to have snuck back up behind him, so his shoulders drop when he realizes that it’s just the bartender.

“You waitin’ for something else?” he asks. “Taking up good real estate if not.” He juts his chin toward the steadily increasing crowd of people looking to apparently drown out the subpar comedy with copious amounts of alcohol.

“Oh. Uh, no,” Cas finally manages to get out. “Sorry.” He gets up from the barstool and heads back to his table, only to find that it’s been taken by another group. Grabbing a spot up against the wall in the back of the club, Cas focuses on enjoying the remaining comics, but no matter how hard he tries, his eyes keep wandering back to one particular visitor at table three.


	2. Chapter 2

Dean Winchester has made himself at home in Cas’ mind, and even though he shows no signs of leaving anytime soon, Cas tries to shove him out with another story, this one about a twenty-something sitting across from him on the train and grinning down at his phone.

_ He just moved to the city, and is heading home from a very promising first date with a goddamn gorgeous stand-up comedian— _

No. Stop it.

Cas rubs his eyes with his thumb and index finger before settling into another story, this one revolving around a kid, maybe in his late teens, holding a plastic bag from a nearby record store in his hands.

_ This kid’s older brother does everything for him, is his only real family member. His brother doesn't have much time for himself, but he loves comedy, so for his birthday, his brother got him— _

“Shit,” Cas breathes. He runs hand through his hair and glances around the train car, trying to find someone,  _ anyone _ , he could create a story about without including Dean fucking Winchester. When the doors open at the next stop, a tired-looking woman in her early thirties enters the train and sits down across from him, stretching her arms high above her head before pulling a book from her bag.

_ She has two little girls at home. She just got off her late night shift at the hospital, and is exhausted, but still excited to see Rachel and Robin...no, Rachel and Amelia. She would normally have to pay for a sitter, but her boyfriend, Arlo, volunteered to stay with them. She loves Arlo, and how ridiculously handsome he is, with his short, messy hair and dusting of freckles across his nose and crooked smile and bright green eyes— _

Fuck.

Cas leans back in his seat with a frustrated sigh, loud enough for the woman next to him to glance over uneasily, then scoot a little further away. He closes his eyes and tilts his head up toward the ceiling of the train, absorbing the way it winds and shudders around curves. After a few seconds, his phone vibrates in his hand, and he slowly pulls his head back to its normal position before unlocking his phone and thumbing over to his texts. There’s just one, from Gabe, and Cas rolls his eyes before he even finishes reading the whole thing.

_ I’ll buy you a beer if you take artistic liberties on how much applause there was tonight _

Another text with six beer mug emojis comes through seconds later, and Cas clicks his phone off. Six beers is nowhere near the amount of alcohol he needs to deal with this.

 

“Cassie!” Balthazar says from the couch when Cas enters their apartment later that night. “Where’ve you been, young man?”

Cas tosses his bag onto the kitchen table before digging through the fridge for a water bottle. He finds a beer first and decides on that instead. “Out,” he says, popping the cap off and taking a long drink.

When he sets the bottle down, Balthazar has moved with more agility than Cas has ever seen during their three years as roommates, and is now standing across the table from him, arms folded expectantly across his chest.

“You’re never just ‘out.’”

“I have plans, Balthazar,” Cas says defensively. “Sometimes.”

Balthazar barks out a laugh. “Understatement, but fine. What  _ plans _ did you have tonight?”

_ Keep it cool, Cas _ . “I covered an open mic night at Gabe’s new comedy club for work. As a favor.”

He almost wants to laugh at the way Balthazar cringes at the words “open mic night,” but decides against it. His roommate emits a low whistle. “Yikes. Amateur comedy. You have my pity,” he says, resting his hand on Cas’ shoulder. “How shitty was it?”

Cas considers this for a few seconds, then shrugs. “Not too bad.”

Balthazar purses his lips, then his eyes widen and he smacks Cas on the shoulder. “Novak, you  _ dog _ !” he says gleefully. “You  _ met _ someone, didn’t you?”

_ Goddamn it. _

“No,” Cas mutters, but he can feel his cheeks heating up already. Balthazar doesn’t listen to him; instead, he leans forward on the table, resting his chin on closed fists and staring at Cas intently, like he’s waiting for the greatest bedtime story known to mankind.

“Go on,” he says, motioning with his hand for Cas to continue. “ _ Regale  _ me.”

“It’s nothing,” Cas insists.

“Was he a comedian? A funnyman?” Balthazar searches for a reaction from Cas, then snaps his fingers. “He  _ was _ ! Is that why you’re pissed at me, because I insulted your boyfriend? Was he funny?”

“He wasn’t bad.”

“What’s his name?”

“De—no, why the hell would I tell you?”

Balthazar grins. “Because if you don’t tell me, you know I’ll find out myself.”

Cas groans and finishes off the last of his beer. “Remind me why I agreed to live with you?”

“My charming personality and dapper good looks.” Balthazar points at Cas. “Name. Now.”

Cas sighs. “Dean.”

“Dean,” Balthazar repeats, testing out the name in his mouth like a fine wine. “What’s he look like?”

_ What’s he look like. He’s fucking gorgeous, and like someone who would have absolutely no interest in me. _

“Handsome. He was mugged a few nights ago and is a little bruised, but I think he’ll heal well.”

“You get his number?”

“I…” Cas pauses. “He was busy. Very busy.”

Balthazar groans and staggers backward as if he’d been shot, rolling over dramatically onto the couch and draping a hand across his forehead. “Are you  _ kidding  _ me?”

“He said it was nice to meet me!” Cas says defensively, while also trying not to mentally berate himself for the same thing Balthazar was chewing him out for. Balthazar stares up at Cas from the couch and shakes his head.

“You disappoint me, Novak,” he says. “So, so much.”

“He was  _ busy _ !” Cas protests.

“Then you get your ass back there tomorrow night when he’s ‘less busy’ and you get that motherfucker’s number!”

“Come on, Balthazar. I’m sure he was just being polite.” Cas can feel his shoulders slump with that admission, something he’d been thinking about since the moment Dean had been pulled away to table three. People that attractive aren’t just  _ interested _ in awkward weirdos like him. It doesn’t happen, and the stupidity Cas feels at even entertaining the thought almost makes him want to puke.

“Yeah, and I’m just a terrible roommate.”

“Actually—”

Balthazar raises a finger. “Enough from you. You’re getting his number, even if  _ I  _ have to get it for you. I refuse to be the one responsible for you ending up forever alone. I can’t live with that on my conscience.”

Cas opens his mouth to answer, but before he can, Balthazar’s on his feet and heading into his bedroom. Cas rolls his eyes and starts rummaging through their cabinets for snacks as he listens to Balthazar typing furiously on his laptop.

“Where was it?” he yells, heading back into the living room while balancing his laptop in one hand and still typing with the other.

“Yuk-Yuk Hut.” Cas pauses. “Wait, what’re you—”

“ _ Jesus _ !”

Cas startles at Balthazar’s outcry, and almost drops a bag of chips as his roommate shoves aside a stack of mail to make room for his laptop on the table. He points dramatically at an incredibly tacky website straight from the 90s—deep purple background, multicolored bubble letters, the words  _ HA HA _ hovering just above the cursor—and draws Cas’ attention to one headshot in particular, underneath  _ THIS WEAKS HEADLINER’S _ .

“Jesus, he needs a proofreader,” Cas mutters, wincing.

“True, but irrelevant,” Balthazar snaps. He jabs his finger at one headshot in particular. “Is  _ this _ your Dean? Dean Winchester?”

“I...yes.”

“You told me he was handsome,” Balthazar says, “ _ not _ that he was a fucking adonis.”

Cas studies the photo, secretly pleased to get another chance to look at Dean, and shrugs. “I suppose it’s possible I might’ve downplayed—”

“ _ I’d  _ fuck this guy,” Balthazar interrupts. He scrolls down the webpage, his eyes scanning the screen. “He’s gonna be there again on Friday night, and if you’re not there, too, I’m kicking you out of the apartment.”

“To go to the show, or for good?” Cas asks, smiling to himself at his roommate’s frustration.

“One, then the other.” Balthazar glares at him, then shakes his head. “You’re going, and that’s final.”

Cas shakes his head and makes his way to his bedroom. “Okay, Mother.”

He closes his bedroom door to try and block out the noise of whatever TV show Balthazar just decided to turn on at full volume, and grabs his laptop before flopping down onto the bed. He opens a new document and worries his lower lip between his teeth as he stares at the blinking cursor, trying to figure out how this entire article isn’t going to end up being about Dean Winchester’s face.

 

**_Laugh House_ **

_ By Cas Novak _

_ As any New Yorker can tell you, this city has no shortage of comedy clubs. _

_ There’s also no shortage of comedians, which is why the Yuk-Yuk Hut is a welcome addition to the city's comedy scene. _

_ Located on 9th Street in Brooklyn, the Yuk-Yuk Hut holds open mic nights every Monday, Wednesday, Friday, and Saturday for locals looking to cut their teeth on the comedy scene. Rebranding itself after a lengthy closure as the club’s management changed hands, the Yuk-Yuk Hut is still getting its sea legs, but for the most part, has come out of the gate strong. A host of local talent was on display, and the club is sure to draw both locals and visitors alike. So if you’re looking for something to do one night that doesn’t involve Netflix (he says as he’s currently marathoning  _ The Great British Bake-Off _ as he writes this), stop by the Yuk-Yuk Hut and take in a laugh or two. _

 

Cas’ article on the Yuk-Yuk Hut runs on the  _ Times _ ’ website the next day, and by lunchtime, it’s gotten a surprising amount of hits, comments, and likes. Billie, the paper’s social media manager, is getting a bit too invested in fielding comments, if Cas is being honest, but he still can’t help being entertained.

Billie laughs in disbelief at a new comment, shaking her head disappointedly. “This asshole thinks Cole Trenton is funnier than Linda Tran, well, he can fuck right off,” she says, and Cas watches as she pulls out her phone and types out a reply to the commenter.

“Can’t you get in trouble for that?” Cas asks hesitantly.

“For what?”

“Just—” Cas gestures vaguely at her computer screen, “—even if you’re using your own personal account to get in arguments online, won’t that come back to bite you?”

Billie smirks. “You think this is my first rodeo?” she asks, tapping her phone screen. “This account doesn’t have my real name on it. No identifying info, no chance of me getting fired.”

Cas raises his eyebrows. “Living on the edge.”

She flips him off before turning back to her computer, and Cas grins. He clicks over to the  _ Times _ ’ Facebook page and checks out the newest comment on his article by an anonymous user referred to only as “The Reaper.”

_ You wouldn’t know good comedy if it bit you in the ass, idiot. _

“Isn’t ‘The Reaper’ a little ominous for a username?” he asks.

Billie rolls her eyes. “Listen, Novak, if you want a cutesy name, you can make your  _ own _ anonymous profile, got it?”

Cas opens his mouth to respond, but before he can, another voice interrupts them.

“Novak.”

Cas looks up to see his editor Zachariah standing in the doorway of his office. He motions for Cas to follow him inside, then closes the door. Cas glances back at Billie, who gives him a smile that’s trying too hard to be positive, and heads for the office.

“Your piece on your brother’s comedy club has gotten some good traction,” Zachariah says, looking at Cas over several stacks of papers on his desk. Cas can swear that his editor almost sounds disappointed. “More than we’d been expecting.”

“I, thank you?”

“I’m going to need you to do a follow-up,” Zachariah says. “We’ve gotten good interactions and comments on socials; it’ll be good fluff content we can throw up for slow news days.”

Cas decides to ignore the backhanded compliment and nods. “Sure. Of course.”

“Great. I’ll expect something by the beginning of next week.”

As Cas leaves Zachariah’s office, a thought strikes him. He needs to write more about comedy. Maybe even get an interview with a comedian. And if he wants to keep the trend going, he should probably talk with someone who performed at the Yuk-Yuk Hut the night he was there.

For continuity’s sake.

Cas makes a beeline past his desk and is already dialing Gabe’s number as he walks out into the hall.

 

“ _ Heeeeey _ , little brother.” 

Cas presses a finger to his ear to and tries to concentrate on his brother’s voice amongst the chaos and noise of wherever he’s located.  “Where are you?”

“Not important. Hold on.” There’s some shuffling and a few crashes that sound alarmingly like breaking glass, then a door closes. When Gabe gets back on the phone this time, the line is relatively quiet. “What’s up?”

“My article on your club was very well-received.”

Gabe whoops over the phone, and Cas can’t help but smile a little in spite of himself. 

“My editor would like me to put together some kind of follow-up, so, ah…” Cas trails off. How desperate would this sound? What are the chances that Dean even remembers him? He must’ve sweet-talked at least ten other people that night, and it’s been a few days, there’s no way—

“Cas, I’m kind of busy here—”

“Can you get me in touch with Dean Winchester?” Cas blurts out, and he can feel the sweat building on his palm against the phone as he tries to stay casual. “He was one of the comedians at your open mic. I’d like to write a profile on him.”

There’s a long pause on the other end, long enough that Cas wonders if their call had been disconnected, but just as he’s about to ask Gabe if he heard him, his brother’s voice comes crackling through once more. “Dean Winchester, huh? You fucking bet I can.”

Cas spends the majority of the subway ride to the Laugh Factory, another comedy club Dean says is closer to his place, trying to come up with excuses as to why he’d have to leave early, or not even show up altogether. It should be easier, considering the fact that he comes up for excuses and reasonings for people as a goddamn  _ hobby _ , but apparently the same rules don’t apply to him. 

The Laugh Factory is practically deserted, only a few employees dotting the floor and preparing for that night’s set. The air is stale with booze and tobacco, and Cas quickly decides that he doesn’t like the quiet, stifling nature of a closed comedy club.

A couple of people glance up when he enters, but no one makes any attempt to help him. Cas scans the tiny room, and it doesn’t take long before his eyes lock on Dean. He unconsciously sucks in a breath when he sees him, sprawled out in a chair, thumbing absently through his phone. Cas watches the way his eyes scan the screen, how its faint glow highlights his jaw, and swallows hard.

_ Fuck _ .

Dean looks up then, as if Cas had said the word aloud, and for a second, his heart seizes with the idea that maybe he had. The comedian’s eyes brighten in recognition, and he pockets his phone before getting to his feet and heading toward Cas.

“Hey,” he says with a grin. “How’s it goin’?”

“Your, uh, face looks better than I was expecting,” Cas says in greeting. He cringes inwardly at just how goddamn  _ awkward _ that was, but that self-beration quickly turns into relief when Dean laughs. It’s a rich, deep sound that Cas immediately feels comforted by.

“Well, aren’t you the flatterer,” Dean says with a smirk. He takes a step back and holds out his arm in an exaggerated permissive stance. “After you.”

Dean grabs them a table in the corner, furthest away from the stage. Cas slides into the seat across from him and glances down at the table; it’s covered in initials and proclamations of love, carved into the wood with silverware or pocket knives. He runs his index finger over the surface and looks up quickly when Dean chuckles.

“Cool, huh? My name’s on table four,” he says.

“Isn’t this vandalism?” Cas asks, pulling out his recorder and setting it on the table between them.

Dean shrugs. “Technically.”

Cas pauses as Dean tips his head back to sip his beer. He watches his throat hitch as the liquid travels down, and shakes his head quickly. “How’s this for a title,” he starts, trying to switch gears and get himself into work mode. “ _ Dean Winchester: Comedian by Night, Vandal...Also by Night _ .”

Dean purses his lips and considers the pitch. “Could be a little snappier,” he says, “but I’ll take it.”

Cas rolls his eyes before looking up at Dean with his finger hovering above the RECORD button. “Ready?”

Dean nods. “Shoot.”

Cas presses the small red button, and they’re off. 

“Okay, so, Dean Winchester. New York City comedian extraordinaire, right?”

“I wouldn’t say that.”

“Then I will,” Cas says quickly, pleased with the way Dean’s cheeks go pink. “I guess we can start with the basics. How’d you get into comedy?”

Dean looks off over Cas’ shoulder, chewing thoughtfully on his lower lip. “My dad, I think. Well, it’s his fault, I guess. I remember being little, like five or six, and him falling asleep in the living room with a Richard Pryor special on.”

Cas raises his eyebrows. “You saw Richard Pryor when you were  _ five _ ?”

“Or six.”

“Oh, well that’s totally different, then. Continue.”

“I dunno. I don’t think I really understood what he was saying, but I remember how happy he made people. He made everyone laugh, and I decided then that that was what I wanted to do, too. My little brother, he helped a lot, even though I don’t really think he realized it. I liked making him laugh when he was scared or pissed off or upset.” He takes another sip of his beer, almost sheepishly, and Cas can’t help but find it endearing. “Not exactly the most original story, but…” He shrugs.

Cas waves Dean’s concerns away. “People will enjoy it. Now, I know some parents are...less than enthusiastic about their kids getting into the arts—mine were, anyway—so how did your parents deal with it? Supportive?”

There’s a pause as Dean takes a breath, focusing on the table. He traces over a few initials gently, almost reverently, before looking back up at Cas. “Uh, no. Not exactly.”

Cas bites his lip and tries to switch topics as quickly as possible. It’s against everything Zachariah would have him do—if there’s more dirt that looks like it could be dug up, you jump in with the biggest shovel you can find, no questions asked—but Cas almost immediately feels protective over Dean. Sure, whatever happened between him and his parents is probably a journalistic goldmine, but for now, Cas sticks to the belief that it’s something that should stay buried.

“Sorry,” he says quickly, flipping through his notebook, trying to find a suitable question to ask next. “Uh...have you always lived in the city?”

“Nah. Born in Kansas. Lawrence.”

“When did you move up here?”

“Seventeen,” Dean says quickly. “My brother and I just picked up and—” He holds one hand out, palm up, and slides the other across it, “—left. Never looked back.”

“Do you have any other siblings?”

Dean shakes his head. “Just him. Sam. Four years younger.”

Cas takes a few seconds to scribble down some more notes, then moves onto his next question. “Do you do comedy full time?”

Dean smirks. “If I did comedy full time, you think I’d be performing in places like this or the Hut?” He gestures around them, then shakes his head.  “I’m a teacher. Elementary school.”

Cas looks up from his notebook. He can’t say why, but he wasn’t expecting that answer. “Really?”

“Second grade. The kids are sweet, and they’re a great audience as long as they get recess. I used to work with cars, but there ain’t as much of a need now that we’re in the city.”

Cas wrinkles his nose unconsciously. “Please tell me you aren’t an English teacher.”

Dean tilts his head to the side, regarding Cas curiously. “And what if I am?”

“An English teacher who says  _ ain’t _ ? Really?”

Dean’s eyes narrow, and he grins. “I wish I  _ were _ just an English teacher, just to piss you off.”

Cas’ eyebrows shoot up in surprise; he hadn’t been expecting Dean to be so blunt with his answer, but for some reason unexplainable to him, he actually likes it.

“So what do you teach, then? A little bit of everything?”

“More or less.” Dean leans back in his chair, lacing his fingers behind his head. “Little bit of vocab in the morning before snacks, then close out the day figuring out who'll have more apples in those stupid math problems.”

“Mhmm.” Cas pauses, then looks up at Dean. “Can I ask a stupid question?” he asks hesitantly. “Off the record, I mean.”

Dean’s ears perk up at that. “Absolutely.”

“Aren't you supposed to say something like, ‘There’s no such thing as stupid questions’?”

Dean waves him off. “To the kids, yeah. But we both know that ain’t true,” he says, putting extra emphasis on the  _ ain’t. _ “So lay it on me.”

“Do they still have those book fairs that come and set up in the gym?” Cas asks. He thinks back to all the times back in elementary school when he would pick out stacks of books and read them under the giant beech tree after school. His first discovered his love of words through the books he got at those fairs, and the idea that they might be gone is sadder than he'd readily admit.

Which is why he's so pleasantly surprised when instead of staring at him blankly or bursting into laughter, Dean’s eyes light up.

“Best day of the year,” he says simply, and Cas laughs.

“I agree.”

“I fuckin’  _ loved _ those things when I was a kid,” Dean says. “Sam and I would save up for months beforehand. He loved ‘em, found some of his favorite books through those fairs.”

It’s all Cas can do not to rest his chin in his hands and gaze dreamily at Dean as he goes into more detail on his favorite series—books like  _ Matilda _ ,  _ Goosebumps _ ,  _ Super Fudge _ ,  _ Harriet the Spy _ —and how he and Sam would stay up late, reading by flashlight under the covers long after their father had gone to bed.

“What about you?”

Cas blinks and looks at Dean, a little confused. “What?”

“You said you loved ‘em, too. What were some of your favorite books?”

“Oh.” Cas pauses for a few seconds, letting the memories of some of his favorite books come flooding back to him. He glances quickly at Dean again, half expecting to see a bored expression on his face, and is almost shocked to see that Dean looks just as invested as he feels.

“There was this one book,” Cas starts, “called  _ The Pigman _ …”

 

Cas isn’t one hundred percent sure when it happened, but somewhere along the line, their interview had turned into a date. Almost everything the guy says further cements himself as, well, Cas’ idea of a perfect guy.

Dean is in the middle of telling Cas about his favorite comic books when one of the club’s employees comes up to their table and knocks on it. He’s young, maybe a college student, and has dark curly hair and thick-framed glasses, and nods toward them. “You guys planning on staying for the show?”

Cas glances at Dean, who shakes his head. “Not tonight, man. Another show, then papers to grade.”

“We’re closing up for a bit beforehand,” the kid says apologetically. “So, uh…”

When Dean purses his lips and nods at the kid’s unspoken request, Cas isn’t sure if the traces of disappointment on his face are just a figment of his imagination, but before he can think too much about it, Dean reaches across the table, grabs Cas’ notebook and pen, and starts scribbling next to his notes. He finishes writing and scans his handiwork for a few seconds before sliding the notebook back to him.

“In case you, uh, need another quote or something,” he says.

Cas looks down at his notebook and back up at Dean, flashing him a grateful smile. “Thank you.”

 

Cas has never programmed a number into his phone so fast.

The subway is crowded, but for the first time in recent memory, Cas has no interest in trying to create a story for anyone else. Instead, he glances down at the newest number in his phone and starts to think.

_ He didn’t think this would happen. All he was expecting was to go out, force himself through some shitty amateur comedy, and write a one-off fluff piece on his brother’s club. This  _ shouldn’t  _ be happening. He never gets guys like this, but no matter how much his self-worth tries to convince him, this isn’t a joke. Soon enough, he might have someone to bring home, someone to support him, someone he could support, too. _

_ He’s happy, and it’s been far too long since he last felt this way. _

_ It feels good _ .

* * *

 

After a solid hour and a half of failed sleep attempts later that night, Cas stumbles out of his room and sprawls out on the couch to try and fall asleep to ridiculous infomercials.

He surfs through a few channels before landing on public access. It looks like there’s some kind of badly organized talk show going on; Cas furrows his brows together and leans a little closer to the TV. The people on stage are reminiscent of a freak show — a guy not much older than Cas is dressed in nothing but swim goggles, a blue bathing suit, and blue diving flippers; someone dressed in a banana costume sitting next to a woman with fairy wings — but what catches Cas’ attention most and keeps it there is one of the panelists.

Who looks a hell of a lot like Dean.

_ He’s everywhere. _

Cas digs the heels of his hands into his eyes and stares harder at the screen. The video quality isn’t great, but it’s definitely him; he’s wearing the same shirt he had on earlier that night. Cas grabs the remote and turns up the volume a few more notches, watching as Dean throws his head back and laughs at something said by one of the women on the panel. 

That’s when Cas notices the words LIVE CALL-IN written at the bottom of the screen, with a phone number. Without thinking about it, Cas heads back into his room, grabs his phone, and starts dialing.

“Cas Novak,” he says absently when someone on the other line asks for his name. His sleep-deprived mind can’t focus on much more than the fact that he gets to see Dean twice in one day, and he zones out, staring at the screen.

The host, a scrawny, nerdy-looking guy with thick glasses tries to calm the panel down. “Hold on, it looks like we’ve got a call. Cas from New York, you’re on the show.” 

Dean perks up immediately at Cas’ name, and he furrows his brows together, focusing on the main camera in front of him.

It takes Cas a few seconds to realize that he’s hearing the host’s voice through his phone, not the TV. He’s on the show, and the idea paralyzes him with fear. 

“Cas, what’s up?” the host asks; he’s trying to stay polite, but Cas can tell he’s a little confused, maybe even annoyed that Cas won’t speak up.

“Dude, we’re gonna have to hang — ”

“Dean?” Cas finally asks, thrown off by the way his voice echoes back at him from the TV. The host swivels in his seat to look at Dean, his eyes bright with curiosity.

“Random Dean, you know the caller?” he asks, grinning.

Cas’ heart clenches at that, and he stares at the screen, waiting for Dean’s reaction. Dean’s cheeks have gone a little pink, but he leans back in his chair, trying to maintain an aura of nonchalance. “Yeah,” he says with a grin. “What’s up, Cas?”

The host looks absolutely  _ delighted _ at the awkwardness that’s now taking place on his show, looking eagerly at the screen and making Cas feel like he’s staring right through him. 

“I, uh, sorry,” he says quickly, and hangs up. Cas can feel his cheeks go hot, even in the privacy of the empty living room, as everyone on the panel laughs. 

He watches the show for a few more minutes, trying to make sense of it all. 

“He hung up?” the host asks. When Dean nods, he turns back around. “Cas, call us back! 212-757-1393, we promise we don’t bite.”

“ _ Fuck _ ,” Cas breathes, leaning back against the couch and running both hands through his hair. He watches as Dean grins at the screen — not at him, not at him, he’s probably looking at nothing get it  _ together _ , Cas — and finally lays down with his face toward the couch. He palms around for the blanket draped over the back and curls up underneath it, letting the sounds of Dean’s show slowly lull him into a restless sleep.

**Notes for the Chapter:**

> The show Dean is on is the [Chris Gethard Show](https://www.youtube.com/playlist?list=PLBDD9FE6F3007B95C), one of my favorite things that's ever graced public access.


	3. Chapter 3

Cas’ neck is killing him, and he groans as he slowly pulls himself back into consciousness. The TV is still playing faintly in the background, and as he slowly unfolds himself from his cramped, awkward position on the couch, Cas realizes he must’ve fallen asleep watching Dean’s show.

He stretches his arms high above his head, and when he closes his eyes, can still picture Dean sitting in on that ridiculous panel; with a glance at his phone, all the embarrassment from his shitty attempt at a phone call comes flooding back.

“Shit,” Cas mutters, reaching for his phone. When he goes to unlock it, there’s a string of text notifications waiting for him; his stomach does a happy little flip when he sees that they’re all from Dean.

_ Dean Winchester, 1:02am: hey, got your number from the show’s caller id. SURE you’re not awake, but if you are, wanna grab a beer? _

_ Dean Winchester, 1:33am: ...or not _

_ Dean Winchester, 3:32am: night, cas _

“ _ Shit _ ,” Cas mutters again, shooting bolt upright, immediately unlocking his phone, and typing out a hasty reply. 

_ Cas, 9:14am: I’m so sorry, Dean, I must have fallen asleep. Rain check on the beer? _

After a second’s consideration, Cas adds a little umbrella and raindrop emoji at the end for good measure. He isn’t expecting a reply right away — especially when Dean’s last text came in so early in the morning — so he locks his phone, turns off the TV, and decides to try and be even the slightest bit productive.

A shower, laundry run, and sink clearing session later, Cas checks his phone and tries to hide his disappointment when there’s still no response from Dean. It’s been hours; he should’ve replied by now, right? If he wasn’t pissed at Cas for leaving him high and dry last night.

Cas closes his eyes and presses a hand to his forehead in frustration.  _ That’s impossible, Cas, stop catastrophizing. I’m sure he’s just busy, he’s just _ _ — _

Cas’ thoughts are interrupted when Balthazar barges into the apartment, humming loudly. “Afternoon, Cassie,” he says cheerfully, setting a bag of groceries on the table before flinging open the fridge and grabbing a beer. “Lovely time for some day drinking,” he says, cracking the bottle open and toasting it toward Cas before taking a swig. When he notices that Cas isn’t responding, he puts his beer down and studies him curiously. “And what’s got your drawers in a twist today, darling?”

“Balthazar,” Cas says hesitantly. “You’re good with, uh,  _ romance _ , right? Flirting?”

Balthazar scoffs. “Good? I’m the  _ best _ , Cassie.”

He heads for the couch and drops down next to Cas. “Now, let’s see how we can get Dean Winchester in your pants.”

“How did you —”

Balthazar looks at him flatly. “If it’s not him, then I’m not helping you.” Cas pulls his phone close to his chest and keeps it there for a few seconds before eventually conceding, handing his phone off to his roommate.

He grabs it and scans the last few texts between Cas and Dean, worrying his lower lip between his teeth. Cas watches him, trying to read his reaction.

“What?” Cas asks. “How bad is it? What should I have done differently?”

Balthazar swats him away like he's an annoying fly. “You,” he says, pointing at Cas, “are a child. He’s an  _ adult _ , he’s  _ busy _ . Sometimes people don’t respond to texts right away. That’s it.” Balthazar looks like he’s about to hand Cas’ phone back to him, but hesitates at the last second. “But if you  _ really _ want my help…”

Before Cas can react, Balthazar’s fingers start flying over his phone screen, and his heart drops in a panic. “Balthazar, n — ”

“Here.” Balthazar presses the phone back against Cas’s chest with a wry grin, and tips an imaginary hat. “That’ll work.”

_ Cas, 2:01pm: Hello Dean, I’m sorry I missed your texts last night, but would very much appreciate the chance to woo you further in person. _

Cas’ eyes go wide. “You’re not serious.”

“It’s what you wanted, isn’t it? For him to respond to you?” Balthazar smirks at that, and Cas wants to be sick. He starts typing out his own messages in response.

_ Cas, 2:02pm: Disregard, that was my roommate _

_ Cas, 2:03pm: Sorry _

_ Cas, 2:03pm: [emoji of monkey covering its face] _

Balthazar peeks over his shoulder and bursts out laughing at Cas’s attempt at damage control. “Good one, Cassie,” he says, clapping his roommate on the shoulder. “Nothing turns a man on like monkey emojis.”

 

* * *

 

Cas looks up from his computer when Balthazar knocks on the frame of his door after dinner. “Any word from our Prince Charming?”

 

Cas shakes his head.

 

“Pity. I’m sure he’ll reply eventually.”

 

Cas waits until Balthazar’s exited his room before flipping him off.

 

* * *

 

“How about now?”

 

“Nothing.”

 

“Odd.”

* * *

 

“Anything?”

 

Cas looks up at Balthazar helplessly, and for the first time since their conversation earlier that day, Balthazar seems just a tiny bit bothered. 

 

“I’m sure we’ll be hearing from him any minute,” he says as he turns up the volume on his cooking show, and Cas can’t tell who Balthazar is trying to convince more, Cas or himself.

* * *

 

“You know what, I’ve had enough of this,” Balthazar says after checking in with Cas one more time. “We’re not in middle school; I’m not letting you sit here moping over a boy all night. We’re leaving.”

“Balthazar, I don’t — ”

“Too bad,  _ I  _ don’t want to hear it. Make yourself presentable; we’ll find someone who appreciates my — _ your _ , your — sensibilities.”

“I’m not — ”

“We’re  _ going _ .”

“Where?”

“DARE.”

Cas wrinkles his nose. “The anti-drug program?”

“The ant — _ no _ . Come on, up.”

 

 

When Balthazar had asked Cas to go to DARE with him, the last thing he’d been expecting was a live storytelling show. 

Balthazar was quick to lead Cas into the Bell House, get them situated at a table, and order drinks for them both. A few stories in, and Cas has to admit, his roommate had been right: listening to stories from other people  _ is _ a good way to get his mind off of whatever the hell is going on between him and Dean.

“Pamela Barnes, everybody!” the host, a short Asian kid who looks like he’s fresh out of college named Kevin says, heading up the steps of the stage and gesturing toward where the latest storyteller, a no-nonsense-looking brunette is giving one more wave before leaving the stage. “I hope you all are ready for a complete 180 here,” he says, “because our next story is a bit of a doozy. Give it up for Dean Winchester!”

And Cas’ heart just about stops.

He can feel Balthazar’s eyes on him, but he refuses to look at his roommate, just shaking his head stubbornly instead. “Dean Winchester” is a common enough name, and New York’s a big enough city; there’s no  _ way  _ this can be the same guy Cas had made a fool of himself in front of just a few days earlier, the same guy Cas saw on fucking public access last night, the same guy who still hasn’t answered Cas’ goddamn texts. It can’t be.

But of course it is.

The very same Dean Winchester bounds up the steps onto the stage, smiles out at the crowd, gives a quick wave, then glances off toward where Kevin had just stepped away. “Kev, can I sit? Cool.” And Dean sits, his legs dangling over the edge of the stage. “Can y’all still see me?” The audience gives its approval, and Dean nods, then wastes no time in launching into his story.

“All right, tonight I’m gonna tell you about my car. She’s a beauty, a 1967 Chevy Impala. Yeah, I see you,” he says with a chuckle, pointing at someone in the audience who apparently had made a noise of approval about the car. “Look but don’t touch, pal.

“Now, that car, that car is my baby. One of the only constants in my life, ever since I was a kid. Hell, she still has Legos jammed into the vents from when my little brother Sam and I didn’t know any better. I had a lot of firsts in the Impala, but the one relevant to tonight is my first fight. 

“One night in high school, I came home with a bruise under my eye,” he says, tapping his cheekbone, not too far from the injury he’d been sporting when Cas first met him. “I’d gotten in a fight in said car, and the last thing I wanted was for my old man to find out. Not because he’s some pacifist who’s against fighting or whatever — he’s a military guy through and through. I didn’t want him to find out because of  _ who  _ I’d gotten in a fight  _ with _ .” 

He licks his lips and takes a deep breath. “But let’s go back a bit further, huh? I’d been dating this girl, Lilith, and things were going good. She was sweet, sex was great — ” That earns a laugh from the crowd, and Dean grins himself, “ — but about a month in, she started finding things wrong with me, I guess, or she’d have issues with things I’d do or not do. Talking to other girls — any girl, any time — got her nails digging into my wrists hard enough to leave a bruise, sometimes even draw blood. Sometimes I’d open the doors for her, but sometimes I wouldn’t, and when that happened, she’d call me over and I’d get a kick to the shin for being inconsiderate. Small shit like that, things that hurt, but still got her message across and weren’t really noticeable by other people.

“One night, though, we got in an argument. One of my best friends is a girl named Charlie, and Lilith never believed that we were just friends. Hell, Charlie had a  _ girlfriend _ , but no, I’m totally cheating on Lilith with her.

“Lilith calls me on it, and it started out as just arguing, but then I guess I said something that  _ really  _ pissed her off, because she punched me. And when I got pissed — as one does after getting punched — she told me that it was my fault, that I made her do it, and I deserved it.” He pauses and surveys the crowd. “I want to tell y’all I knew that was a crock of shit, that I left and never went back, but DARE isn’t a place for fictional stories, now, is it?”

Dean won’t look at anyone, letting his legs swing back and forth in the silence, and Cas is unable to take his eyes off him. He releases a breath he hadn’t realized he’d been holding, and waits for Dean to continue his story. “I was with Lilith for five more months, and every other day, there was something else wrong with me. Once she realized she could get away with it, she snuck in a few more face shots whenever I’d say anything to make her mad, and used to tell me that with all the bruises and fat lips, no one would want to look at me and my fucked-up face, except for her, because she loved me. And I believed it. I couldn’t tell you why, but I did.

“When my old man finally found out…” Dean’s voice trails off, and he grins humorlessly down at the side of the stage. “The — ” another pause, “ — Lilith wasn’t the only one I had to worry about hitting me.” He huffs out a quiet little laugh. “I thought I’d done a good job of hiding it, and if anyone noticed or commented, I had excuses ready. But I must’ve been limping or something when I came home one night, because he called me on it. He didn’t believe any of the old excuses I’d thrown his way before.”

Dean clears his throat, and Cas watches as his eyes dart back and forth, as if he’s expecting someone to run out and force him off the stage any minute. “He didn’t let it go, and when he found out what happened, what had been happening, he wasn’t happy.

“All of a sudden, I wasn’t just his kid anymore, I was a disgrace, an embarrassment, a pussy. He was so ashamed of me, that he didn’t even ask if I was okay; Sam was the one who did that. He was the one who noticed, I guess is the best way to put it. And he got me ice, put up with my trying to come up with excuses for Lilith, and just, I don’t know, was  _ there _ , you know?

“Like I said, Lilith and I did eventually break it off, and as days and months passed, my dad started forgetting about it all. I wasn’t a pussy or a disgrace or a weakling anymore; I was back to being just ‘kid.’ And eventually, I got over Lilith, and started trying out dating again. Which is when I met Aaron.

“Aaron,” Dean repeats, shaking his head, “Aaron, guys, was amazing. We met at school, and from the second he sat down next to me and smiled, I was a fucking goner.”

Cas shifts uncomfortably in his seat, trying to ignore the fact that Dean’s praising another man so reverently in front of a couple hundred people. He glances toward the bar, wondering if he could sneak in a quick refill to help drown things out, but decides against it as Dean continues his story.

“We were together for a couple months, and it was as pretty damn close to perfect as a high school relationship can be. He was sweet and didn’t push things, and understood that I still needed to play the straight card, at least at home. 

“So he would come over and we’d stay in my room. We said we were working on homework or playing video games, but let’s be honest, we were just feeling each other up with Super Smash Brothers in the background to drown out the noise.

“And one day, we were inevitably too loud, and we didn’t hear my dad open the door. I probably wouldn’t have noticed at all if Aaron hadn’t froze up with his tongue halfway down my throat after seeing him standing in the doorway. My dad, he, uh, he wasn’t happy.

“And this time,” Dean says, “he went one step further to show me that. It was bad enough that I’d gotten beat on by a girl before, but being in a regular, stable relationship with a guy? That was even worse.”

Dean closes his eyes and shifts his lips over to one side of his face, trying to get himself together enough to keep going. “He was actually calm at first. Pissed as fuck, yeah, but calm, which just made him even more fucking terrifying. He told Aaron to leave, and once he heard the front door close — ”

Dean doesn’t say anything; instead, he smacks his open palm hard against the stage.

“‘Fucking  _ faggot _ .’”

Smack.

“‘That bitch turn you gay? You’re too scared to be with a woman now, that it?’”

Smack.

“‘No son of mine will  _ ever _ — ’”

Smack.

Dean studies his palm for a few seconds. The tension filling the Bell House is palpable, and he licks his lips before continuing. “It went on like that for a few minutes, I guess. I blocked most of it out, but he was loud enough that Sammy heard him. He came in a little bit after our old man left my room, slammed the door behind him, and damn near burst into tears.”

This time, Dean switches his focus to the ceiling, letting his head tilt back and exposing the long column of his throat to the audience. Cas watches as he swallows, and unconsciously grips his beer bottle tighter.

“Killed me seeing Sammy like that,” he continues. “And knowing it was because of me. Well, because of something that  _ happened _ to me. 

“But he didn’t stay that way for long. I tried to calm him down, make him feel better, but Sammy got  _ pissed _ . He’d had it. He and our dad, they weren’t on the best of terms anyway, but this just sealed the deal for him. He told me we had to leave. No other option; he even had a damn bag already packed.

“And this is where we go back to the car, because once our old man fell asleep that night, my brother and I, we grabbed everything we could, packed up the Impala, and left. We had five hundred bucks to our name and nowhere to go, but we also didn’t have to worry about him anymore.” He pauses, then adds, “We haven’t been back since.” The room fills with applause and cheers, and Dean flashes them all a smile that betrays the pride he’s trying to keep under control.

“We didn’t really have much of a plan; I just picked a direction and drove while Sam slept, then we switched off. For a while, we didn’t have enough for an apartment, or even a shitty motel. We had nowhere to go, so we’d spend the days at the library, late-night cafes, anywhere that’d have us, and then we’d drive to a rest stop or all-night diner, park the car, and sleep there.

“There was no going back, though, even though sometimes I considered it, turning the car around while Sammy was asleep and going home, making sure our dad didn’t take anything out on Sam. But I just kept replaying his face in my head, how upset and scared he was, and how fucking  _ terrified _ I was, and I kept going. Driving became like a reflex after a while; we never took a glance at a map or anything, until we got here, and it felt right. I mean, what better place to start over than New York City?”

A few members of the crowd whoop at that, and Dean smirks. “Yeah, yeah, but this ain’t some buddy comedy road trip movie where moving to the big city suddenly cures all our fucking problems. I’m not gonna lie to y’all, it fucking  _ sucked _ . It did. Those books and movies that glamorize being poor as shit? Don’t believe ‘em, I wouldn’t wish all the shit we had to deal with on my worst goddamn enemy. I could only work so much while studying for the GED, and with all his classes and college prep, Sammy didn’t have time to work at all.”

There’s another pause, and Dean worries his lower lip between his teeth. “But we did it,” he says, sounding like he’s just now coming to the realization himself. “Sammy’s at NYU on his way to becoming a doctor — ” more applause “ — and I’m runnin’ around at one in the morning slinging jokes for tourists, so, you know, we’re both kicking ass.” The crowd laughs at that, and Dean grins.

“I’d probably still be back in Kansas if it weren’t for Sam,” Dean continues. “I’d probably still be letting my dad run my life if he hadn’t stepped in and made me realize that I could run my own. He’s not here tonight, so I can say this without him findin’ out, but he’s my best friend, and if I’m being honest, I think I kind of owe him everything. So, Sammy, this one’s for you.”

The room is silent as Dean slowly gets to his feet, then nods at the audience. “Thanks.”

The second the word leaves Dean’s lips, the entirety of the Bell House bursts into applause. Dean’s cheeks go red and he grins down at his boots, exposing the shyness and anxiety that he’d hidden so well during the actual story.

_ Everybody has a story _ .

And Cas got Dean’s completely wrong.

Cas doesn’t realize he’s not clapping until Balthazar elbows him hard in the arm; he glares at his roommate, but obliges, turning his focus back on Dean. Kevin hurries up the steps and wraps Dean in a hug, something that makes Cas grin because of their height differences, but also ignites a small spark of jealousy he’s not prepared to feel.

There’s another storyteller up next after Dean, but Cas can’t remember a word she says, his thoughts still focused on Dean and his story, all the shit that had gone on in his life. His breath keeps catching in his chest, no matter how hard he tries to push it out.

“Well, he sure gave you a lot to unpack on your first date, eh, Cassie?” Balthazar asks, ribbing him once more with a smirk.

“Shut up, Balthazar,” Cas grumbles, toying with his beer bottle and wishing it wasn’t empty. 

This show can’t end fast enough.

  
  


There’s a line of five or six people waiting to talk with Dean after the show. Cas wants to shove past them all in a classic  _ I’m with the band _ fashion, but when Dean envelops the woman he’s currently talking to in a hug, her shoulders shaking, he decides these people telling Dean their stories is more important than his potential love life.

When the guy in front of Cas shakes Dean’s hand once more before leaving, Cas catches a glimpse of how exhausted Dean looks, maybe not physically, but emotionally. He keeps a smile on until the guy is out of his eyeline, then almost immediately lets his face fall. He closes his eyes and rubs a hand over his mouth; Cas waits for him to acknowledge that he’s ready for the last person in line, trying hard to tamp down the nerves that are making his stomach flip like when he met Tom Baker as a middle schooler.

Dean opens his eyes, and Cas is almost tempted to turn around and pretend he was never here, but when he sees the way Dean’s face brightens when he registers who he is, he’s suddenly rooted to the spot.

“Hey!” he says, leaning forward and enveloping Cas in a one-armed hug. “What’s up?”

“I...nothing,” Cas falters. “I wasn’t expecting to see you here.”

Dean pauses at that, and suddenly seems to have remembered where they are. He sucks in a sharp breath through his teeth. “Most of the shit I said up there’s probably more appropriate for the third or fourth date, huh?” he says.

Cas smiles at him, relishing the way Dean’s eyes crinkle up at the corners when he smiles back. 

“Are we on a date?” he asks.

Dean waggles his eyebrows. “You tell me.”

Cas can feel the blush rising up his cheeks, and he averts his eyes, trying to fight off the impending awkwardness. “I’m, uh, I’m sorry about everything you went through.”

Dean waves the apology away nonchalantly, but Cas can tell Dean is still a bit shaken up after sharing his story. “Been tryin’ to get on this show for months now,” he tells Cas, deftly changing the subject. “It’s always booked up, but I finally managed to sneak into a slot.”

“That’s great.” Cas had no idea it’d be difficult to land a spot on a storytelling show, but Dean seems pleased, and Cas can’t help but echo the feelings.

Dean snaps his fingers suddenly. “Hey, uh, sorry if it was creepy of me to get your number from the show,” he says.

Cas flushes, thinking back to the embarrassment of his virtual stage fright from last night. “They seemed to know you,” he says slowly, “so why did they call you Random Dean?”

“Nobody had any idea who I was when I first started on the show. Every 15 weeks, they hold auditions for a new ‘random,’ and the only prereq is that no one on the panel knows who you are. I’m on week 12 now.”

Cas pauses. “So I could be Random Cas?”

“Hell, yeah, you could. Maybe you’ll inherit the throne once I’m gone.” He grins before glancing down at his feet. “So, uh, I know you didn’t come because I was here, but still — thanks for coming.”

Cas smiles back, his mind racing with whether or not he should confront Dean about his pathetic communication skills.  _ Relax, Cas; he hasn’t pushed you away yet, you’re fine. A misunderstanding. He doesn’t hate you, he  _ hugged _ you, for Christ’s sake. _ “I’m glad I got to see it,” he finally says.

“Text me sometime, huh? We’ll hang out.” 

Cas’ jaw nearly drops open at that, but instead of saying anything like he knows he should, he just nods, gives Dean one more smile, and walks away to meet Balthazar outside.

He’s just shoved open the door when he feels his phone vibrate in his pocket.

_ Dean Winchester, 11:42pm: Why the FUCK didn’t you mention this two minutes ago?!? _

Then, a few seconds later:

_ Dean Winchester, 11:42pm: Woo me, you asshole. _

  
  


“I  _ knew _ he’d come around!” Balthazar says triumphantly. “Where are you two going?”

“The Farmacy,” Cas answers as he shrugs into his jacket. “It’s an ice cream shop. Gabe likes it, which I suppose is no surprise.”

Balthazar purses his lips and nods. “Farmacy’s good,” he says. “Hipster as fuck, but good. Did he choose, or you?”

“Him.”

“Ooh, a man who takes charge. I like it.”

Cas furrows his brows and glances uncertainly at his roommate. “Am I the one going on a date with him, or you?”

Balthazar rolls his eyes and starts to shoo Cas out of the apartment. “Get out of here, Cassie. Don’t do anything I wouldn’t do.”

  
  


It’s colder than Cas had been anticipating, but the hug he gets from Dean a few seconds after they spot each other outside the restaurant is more than enough to warm him up.

“I knew that text wasn’t from you, y’know,” Dean says as they pull apart, and it takes Cas a second to realize that Dean’s referring to the flurry of apology and explanation texts he sent seconds after Balthazar’s.

“I wanted to make sure,” Cas says, “since I never heard from you and all.”

His tone is teasing, but Dean still rolls his eyes. “Christ, I was spending all day trying not to puke from nerves about spilling my guts on stage later that night, but  _ sure _ , make me the asshole.”

The two of them put in their names on the waiting list, then sit down outside on a white metal bench that Cas thinks looks too weak to hold them both, but Dean drops down onto unceremoniously. Cas clasps his hands in his lap, taking care not to sit too close to Dean, but when Dean’s arm drapes over the back of the bench and around his shoulders, he can’t help leaning into the touch.

  
He knows he should be putting all of his focus and attention on Dean, on trying to, well,  _ woo him _ , but in an attempt to tamp down his anxiety, Cas latches on to a college-aged kid standing across from them, leaning against a light pole and smoking a cigarette.

_ He shouldn’t be smoking. His mom, uncle, and both maternal grandparents died from smoking complications, but he was young and rebellious, and now he’s got a habit. His therapist says he’d get the same effect of smoking if he just took deep, regulated breaths, but he doesn’t believe her. _

_ He’s just getting over a breakup, and met someone online, who he’s waiting for now. He wouldn’t admit it, but he’s a little nervous, even though he knows this won’t be anything more than a one-night stand. He’s got to be up and back to campus for class in the morning, after all.  _

_ Moving to New York has been a dream since high school, but he’s not sure how well he’s handling city life. It’s more overwhelming than he’d expected, and _ —

Suddenly, a hand — Dean’s hand — is waving in front of Cas’s face, and he looks up, startled. 

“You know him?” Dean asks, tilting his chin up toward the kid.

Cas shakes his head. “Why?”

Dean shrugs one shoulder. “Looked like you were trying to place where you knew ‘im from.”

Cas pauses, wondering how weird or creepy Dean would find his hobby.  _ Fuck it, he’ll find out sooner or later _ . He sucks in a quick breath through his nose, and takes the plunge. “Sometimes when I’m waiting for something, like how we were just waiting for our seats to open up, I, uh, I make up stories. For strangers around me.”

Dean’s perusing the cheap paper menu the hostess had given them to look over while they waited, but Cas doesn’t miss the way he raises his eyebrows without looking at him. “Like backstories?”

“I suppose. Yes.”

“Huh.” Dean sets the menu down. “So this is like, a hobby or something?”

Cas shrugs. “It’s a good way to pass the time,” he says lamely.

“You do it with everyone?”

“Not  _ everyone _ ,” Cas says, and he can hear the defensiveness in his voice loud and clear even before Dean laughs. One side of Dean’s mouth quirks up in a grin, and his eyes glimmer with playfulness when he finally looks up at Cas. 

“What was mine?”

Cas’ spine stiffens at the question; he closes his eyes and clenches his teeth together to try and maintain some semblance of casualness. Dean laughs again, that rich, warm sound, and nudges Cas with his shoulder. “I know I had one,” he says teasingly. “You don’t exactly have the best poker face, Novak.”

Cas tries desperately to lock eyes with a hostess to find out how much longer they’ll be waiting for a table, excuse himself to the bathroom to have a panic attack, fake his death,  _ some _ thing to avoid having to answer this question. Instead, though, he surprises himself with the smoothness with which he answers. “I come up with stories for every other person I see. What makes you think I remember yours? You’re not  _ that  _ memorable, Winchester.”

Another laugh, one that’s enhanced by Dean throwing his head back. “Fuck you, I’m not memorable. Tell me, or I’m leaving.”

“You were...effortless,” he finally says. “Everything about you. Your day job was very physical, a mechanic or construction worker, maybe. You didn’t have much, but you worked hard for what you did have. You were a provider, a single father with a daughter at home, asleep, and this —comedy— was one of the few things that made you feel alive. You…” Cas’s voice trails off and he tugs on his lower lip with his teeth, wondering if he should continue. “You probably had women fawning all over you, throwing themselves at you left and right.

“But I know I was off, I mean, after hearing everything from last night,” he says by way of apology. Dean waves him off.

“No daughter, that’s for sure,” Dean chuckles. He cracks his fingers on the edge of the bench. “I didn’t think I’d know anyone in the audience,” he continues. “I know it‘s a lot to take in after only knowing each other a few days.”

Cas looks at him, trying and failing to hide the incredulous look on his face. “Are you really apologizing to me for the abuse that  _ you _ went through?” Cas asks.

Dean chuckles. “Guess so,” he says, scooting a bit closer to Cas and closing up what little space remained between them. 

“I’m sorry,” Cas says suddenly, and when Dean looks taken aback, he quickly clarifies. “For everything that happened to you. My parents were...not enthusiastic hearing I was gay, but they never hit me.”

Dean sighs. “One in a million, that John Winchester.”

Cas doesn’t like how lightly Dean seems to be taking an incident that’s entirely appropriate for therapy, but he also doesn’t feel comfortable butting into something he just learned about last night, so he decides to match Dean’s tone. “It certainly seems that way.” He hesitates before adding, “I’m glad you and your brother got out of there, though.”

The corner of Dean’s mouth quirks up in a small smile that he points toward the sidewalk. “Yeah,” he says, cupping his hand a little more firmly around Cas’ shoulder. “Me, too.”

  
  


With its vintage countertops, vinyl seats and booths, and specials written on chalkboards in handwriting that’s definitely the product of ridiculously expensive calligraphy classes, the Farmacy absolutely lives up to Balthazar’s description of “hipster as fuck.” A quick glance through the menu, and Cas also realizes exactly why the place holds a special spot in Gabe’s heart, as well.

Once they’ve ordered their sundaes, Dean and Cas slip into a rhythm of conversation that Cas hasn’t experienced in, well, too long. He still stumbles over words sometimes and takes pauses that are too long, but Dean doesn’t do anything to make him feel self-conscious about it. 

They talk more about comedy, books, and the differences between writing fiction and writing jokes. Cas can’t believe after learning that Dean’s favorite author is Vonnegut that he’s never read anything by Saunders; Dean is deeply offended that Cas has never seen  _ Monty Python _ (and suggests that they get together to watch it sometime). As he takes a sip of his water, Cas feels like they’re in the back of the Yuk-Yuk Hut again, and grins down into his glass at the thought that that first night wasn’t just a fluke.

It'll be like this every time he talks to Dean, and he thinks he can get used to that.

When their waiter finally places a Cookie Monster-themed sundae on the counter in front of Dean, he looks at it like the man had just given him the world.

Cas isn’t sure, and it might be too early to tell, but he thinks he might look at Dean that way, too.

  
  


“Shit.”

Cas and Dean watch as it storms outside, raindrops running down the oversized glass windows of the Farmacy, with no signs of letting up soon.

Cas is calculating how far away it is to the closest subway stop when, out of the corner of his eye, he notices Dean turn sharply in his direction. 

“What're we gonna do?” Dean asks. He looks Cas up and down, a subtle smile playing on his lips.

“I don't know,” Cas says. The rational side of him is about to tell Dean he'll call an Uber, but he keeps his mouth shut as Dean leans in closer.

“Looks like we're stuck here.”

“Looks like.” Cas knows what Dean’s hinting towards, but he still doesn't want to believe it, not when his back is pressed up against the wall, when Dean’s hands are resting on his hips, when Dean’s tongue darts out from between his lips. 

Once Dean’s lips press against his own, though, Cas lets himself believe it. Cas rests his hands on Dean’s hips as Dean’s travel to the small of his back, just barely there, but enough to make Cas’ entire body go hot.

They kiss long and slow, and Cas feels like sparklers are going off inside him; he pulls Dean a bit closer and grins against Dean’s lips when the other man’s breath hitches in pleased surprise.

Cas is seconds away from getting lost in it when he remembers they're standing in the entrance to a fucking ice cream shop, hardly the most romantic place to get down. He forces himself to break the kiss, but smiles at the content little grin Dean’s got on his face.

It's like he's doused with a bucket of ice cold water when he turns around to see a couple behind them, presumably waiting to leave.

“Oh, no, I'm — ” Cas stammers, barely able to make eye contact as Dean starts to move out of the way.

The woman waves him off. “Get it, hon,” she says, waggling her eyebrows and grinning as she traipses by. The man follows close behind and flashes them a thumbs up; Cas smiles when he hears Dean laugh.

“I  _ was _ gonna try to swing by the Comedy Studio for their open mic in an hour,” Dean says, “but I think I've already put on enough of a show, huh?”

Cas grins at him. He opens his mouth to reply, but closes it quickly after thinking better of it; unfortunately, Dean notices.

“What?”

“What?”

“Don’t think I missed that; what were you gonna say?”

“It’s embarrassing,” Cas mutters, craning his neck to see if it’s stopped raining.

Dean laughs. “More embarrassing than sucking face in front of two strangers without realizing it? C’mon, what?”

Cas hesitates, then sighs. “I was going to say that I’d be up for an encore.”

Dean stands there for a few seconds, blinks, then shakes his head. “Yeah,” he says, “I shouldn’t’ve asked you.”


	4. Chapter 4

Cas is in the shower when inspiration suddenly strikes.

He’s been working on  _ One on One _ for almost two years, and despite being almost done with 90% of it, he’s been stuck on a pivotal scene for months. His main character, an eccentric artist named Jackson, is at a crossroads after walking in on his husband with someone else, a woman from his work. Cas had thrown his life into turmoil after that, dragging him down with job loss, near homelessness, and a medical emergency (or three). His luck is shitty enough, but Cas wants something more, a real conflict that doesn’t have a simple solution.

He stumbles out of the shower and just barely remembers to dry off his hand before grabbing his phone and writing out a quick text to his sister, Anna.

_ Cas, 7:34am: What if I give Jackson a kid? _

He’s just hit “send” when soap suds start dripping down into his eyes. “Shit, shit,  _ shit _ ,” he breathes, squeezing them shut before setting his phone on the vanity and hopping back into the shower. He hears his phone chime over the spray a few minutes later and smiles to himself. He knows this is it, it’s what he’s been looking for, the last piece to Jackson’s puzzle he’s been spending ages trying to figure out, and he knows that Anna will think the same.

It’s perfect.

Once he’s toweled off and wiped away some of the condensation on the mirror, Cas grabs his phone and unlocks it to see just how perfect Anna finds his idea.

_ Dean, 7:38am: ...I mean, if you want _

_ Dean, 7:40am: Should I be concerned about Jackson? _

_ Dean, 7:41am: Or the fact that you wanna give him a kid? _

Cas’ stomach drops out, and he leans heavily on the counter, staring down into the sink. He opens up his texts and realizes that his threads to Dean and Anna are right on top of each other, and that Dean had been the accidental recipient of the solution to his writer’s block woes.

_ Cas, 7:59am: Shit, sorry. Just a new story idea. Jackson’s not real, neither is his kid. _

_ Dean, 8:02am: You’re a writer? Like, not just news shit? _

_ Dean, 8:03am: Not that news writing is shit _

_ Dean, 8:03am: It’s not _

_ Dean, 8:04am: but still _

_ Dean, 8:05am: can i read it sometime? _

 

And just like that, Cas finds himself with a new editor.

Dean’s enthusiasm for Cas’ writing comes as a surprise. He wants to be the first person to read anything new Cas writes, even if it's just a sentence or two, and despite his initial reservations at letting _ anyone _ read his writing, let alone someone he’s trying so hard to impress, Cas quickly falls into the habit of integrating Dean’s opinions into his editing routine.

_ Write a scene, give it to Dean, check out his edits, make it better. _

When Cas tells Dean that he shouldn’t feel obligated to look over his work, Dean waves him off.

“It’s nice having a writer boyfriend.”

_ Boyfriend _ . For a few seconds, Cas wonders how long that term’s applied to him. Since the kiss? Sooner? Later? How many opportunities to call  _ Dean _ his boyfriend has he missed?

A few moments later, when he sends Dean a relationship request on Facebook, he decides that he’ll just have to make up for lost time.

* * *

 

When Dean insists on taking Cas out to eat a few weeks later, he’s expecting something like Shake Shack, or maybe even some slices of dollar pizza or falafel. He’s never been to Dean’s apartment, but Dean’s described the tiny studio above a tattoo shop in Jackson Heights, texted Cas in the middle of the night panicking about being a few days late with the heating bill—Cas can tell financial security isn’t on Dean’s radar. 

So when Dean has them get off the subway and start walking toward the Gramercy Tavern, he starts to wonder if one of his boyfriend’s hobbies is to dine and dash.

“You ever eaten at the Gramercy before?” Dean asks.

“No,” Cas says hesitantly. “I never really thought I would.”

“Well, then tonight’s your lucky night.”

“Dean, the Gramercy is expensive…” Cas trails off, and cringes inwardly at the way Dean stops in his tracks, hand pressed to his chest and looking absolutely crestfallen.

“Are you saying,” he says slowly, “that you don’t think I can afford to take my boyfriend out to eat at a fancy joint?”

The fact that he refers to the place as a “joint” is answer enough for Cas, but before he can voice that, Dean continues, “Because you’d be right.”

“I’d be—Dean, I don’t want to go bankrupt over a  _ dinner _ ,” Cas says.

Dean rolls his eyes. “I don’t need fancy food and restaurants with fucking dress codes to impress you, Cas, if that’s what you’re thinking,” he says, then ghosts his hand over the small of Cas’ back. “I can do that myself.”

Cas’ cheeks go hot at that, and he glances back at Dean, who smirks, his eyes narrow. He opens the door to the Gramercy and makes a sweeping  _ after you _ gesture. “I just want a good meal, and we can swing that here. Trust me.”

Cas imagines everyone’s eyes on him as their hostess leads them through the restaurant to their table. He knows he's being ridiculous—they don't stick out  _ that _ much—but he can't help feeling relieved when they're finally seated. He opens the menu and immediately starts scanning the items in an attempt to calm down, a fruitless effort when he realizes that the prices are just turning his anxiety up a notch or seven.

“Jesus, Cas, relax,” Dean says. “I got this.”

“Appetizers here are twenty dollars,” Cas hisses.

“Not for us.”

Cas sets his menu down, fully prepared to give his boyfriend a lecture on how fucked up dine-and-dash is, when their waiter interrupts them.

“Dean, hey, brother.” Cas looks up to see a burly man grinning and shaking Dean's hand. He looks familiar, but Cas can't place where he’s seen him until—

“Benny, tell Cas we're not paying twenty bucks for goddamn hummus,” Dean says.

Benny scoffs. “Surprised  _ anyone _ pays that much for it,” he says, “but you’re covered.”

He takes their drink and appetizer orders, and Dean leans back in his chair, fingers laced behind his head, grinning at Cas. “Perks of having comedian friends,” he says. “We all have shitty day jobs, but most of ‘em come with good discounts.”

“And comedians aren’t anything if not generous,” Cas says, narrowing his eyes.

Dean sits back up straight and points across the table at him. “Exactly.”

When Benny returns with their drinks a few moments later, he sets Cas’ down with extra reverence. “Dean’s taken advantage of my employee discount here more times than I can count,” he says, “but this is the first time he’s brought someone with him. You must be a special one.”

Cas’ eyes dart immediately toward Dean, whose cheeks have gone dark red. “Jesus, Benny,” he mutters, rubbing the back of his neck in embarrassment. “Warn a guy before you’re about to make a fool of him, huh?”

Benny just laughs and winks at Cas. “Let me know when you’re ready to order.”

Cas keeps his eyes on Dean until his boyfriend finally looks at him, still a little sheepish. “Is that true?” Cas asks. “That you’ve never brought anyone else here before?”

Dean shrugs. “First time for everything.”

Cas smiles at him and raises his glass. “To first times.”

Dean grins back. “Cheers.”

 

By the end of the night, the Gramercy has become one of Cas’ favorite restaurants, and, although he’d never say it out loud just yet, Dean has solidified himself as one of Cas’ favorite people. They ate too much and drank even more, but instead of heading for the subway, they decide to walk.

As they walk hand in hand, Cas revels in the way everything seems brighter and moving in slow motion. The rational side of brain insists that it’s just the booze, but Cas prefers to think of it as a side effect of the fact that for the first time in what seems like ages, he’s happy. He’s happy, and he’s making someone else happy.

He likes it.

Dean leads them to a bench on the edge of a park, and for a few minutes, the two of them don’t do anything but look up at the sky, trying to spot even the faintest glimmer of stars through the New York smog. Cas rests his head on Dean’s shoulder, his stomach flipping in excitement when Dean pulls him closer, his arm draped across his shoulders.

“It’s called ‘sonder,’ by the way,” Dean says suddenly, and Cas glances up at him. 

“What’s called what?”

“That thing you told me you like to do, make up stories for people,” Dean says.

Cas wrinkles his nose. “So I’m...sondering?”

Dean opens his mouth to respond, but quickly closes it after thinking it over. “It’s not—no, hold on.” He pulls out his phone—thankfully, without having to take his hand away from around Cas—and starts thumbing through it. “Look,” he says, turning the phone toward Cas. Cas leans in a bit closer to the tiny screen.

_ Sonder: The realization that each random passerby is living a life as vivid and complex as your own—populated with their own ambitions, friends, routines, worries, and inherited craziness—an epic story that continues invisibly around you like an anthill sprawling deep underground, with elaborate passageways to thousands of other lives that you’ll never know existed, in which you might appear only once, as an extra sipping coffee in the background, as a blur of traffic passing on the highway, as a lighted window at dusk. _

Cas looks up when he finishes reading to see Dean looking at him expectantly before turning the phone back toward himself. “See? Sonder.”

Instead of answering, Cas just keeps looking at Dean and the way the faint glow of his cell phone lights up his face, brightening his eyes and emphasizing the sharpness of his jawline.

“It’s beautiful,” Cas says softly.

Dean plants a kiss on Cas’ temple. “Thought you’d like it.”

Cas doesn’t bother to correct him.

* * *

 

Cas could get used to this.

It’s nothing special, when he really thinks about it; if someone looked in and saw them, there wouldn’t be anything particularly interesting to see. He’s sitting on the couch with his laptop, typing away at the latest draft of his book, while Dean’s resting his feet across Cas’ knees, right up against the lid of his laptop, scribbling down setups and new joke ideas in his notebook. 

It’s a little cramped, but Cas ignores the cramps in his legs, smiling down at his keyboard and sneaking glances at Dean’s face, lips pursed in concentration, eyes dark from lack of sleep.

“What’re you doing tomorrow?” Dean asks, looking up suddenly. “Bobby’s out of town, so the open mic ain’t happening. Didn’t know if you wanted to go out or somethin’ instead.”

“I can’t,” Cas says, and the second the words leave his mouth, he knows he said them a little too quickly.

“Yeah?” Dean asks, raising an eyebrow. “Why’s that?”

“I have a...class.” Dean doesn’t even need to ask; he just raises that one goddamn eyebrow a tiny bit higher, and Cas sighs. “An aerial yoga class.”

This time, both Dean’s eyebrows shoot up in surprise. “Aerial yoga?”

“I had a Groupon,” Cas mumbles.

Dean purses his lips, considering him. Cas is sure that Dean’s about to burst out laughing, maybe write down some ideas for jokes at his expense, so he has a hard time hiding his surprise when Dean flips his notebook closed and asks, “Need a date?”

“This is supposed to hold me up?” Dean asks, tugging on the deep blue silk hanging from the ceiling. He cranes his neck back to look up at the carabiner holding the silk in place, then looks skeptically at Cas. “You want to kill me.”

Cas shakes his head. “They’re able to support up to 500 pounds,” he says, flattening out his palm and pressing it into the silk, just like he’d seen in one of the fifty aerial yoga for beginners videos he’d marathoned last night. “We’ll be fine. And besides, you didn’t  _ have  _ to come.”

Dean stares at Cas for a few seconds, then narrows his eyes. “If you think I would’ve passed up the opportunity to see my boyfriend in yoga pants—”

“Dean!” Cas’ cheeks redden almost immediately, and he smacks at Dean’s arm in an attempt to get him to shut up. “Jesus.”

Dean throws his head back and laughs as he heads toward the door. “Save my spot, I’ll be right back.” On his way out, he smacks Cas on the ass. Cas claps his hands over where Dean had hit him, glaring indignantly as Dean leaves the room.

He hopes he hadn’t been too obvious in how much it had turned him on.

 

“Grab six handfuls of your silk,” their teacher, a slim brunette named Lisa says, her eyes scanning the room to make sure everyone’s still with her, “pull the silk down, and as gently as you can, ease yourself into a sitting position inside it.” 

Cas doesn’t have much of a problem with this; he pretends he’s slipping onto a swing, and is sitting comfortably a few seconds later. His feet dangle a few inches off the ground, and he swings them gently back and forth.

“ _ Fuck _ ,” Dean breathes next to him, and Cas grins to himself. He glances next to him; Dean’s managed to get himself into the silk, but instead of sitting still, he’s spinning in place. He tries to reach down and drag a toe along the floor to stop himself, but he can’t do so without slipping out of the silk.

“DId you slide in, or was it more of a hop?” Lisa asks, coming over to Dean and bringing his silk to a stop. She winks at him and walks back to the front of the room before he can answer. “Slide, don’t hop, guys.”

She climbs effortlessly back into her silk and looks out at them all. Cas hears Dean mimic, “Slide, don’t hop,” under his breath, and grins.

“This might look a little hard,” Lisa says, and Dean scoffs again, “but just take your time, and if something feels uncomfortable, don’t push yourself.”

Without another word, Lisa grabs the silk like she’s holding on to the sides of a swing and leans back, lacing her legs above the silk. She keeps leaning, back, back, back, and Cas vaguely wonders if she’s going to hit her head on the ground when she snakes her legs around the silk where her hands were and lets herself drop, her head hovering a few inches above the ground, the backs of her hands resting gently against her yoga mat.

Cas’ eyes widen as he looks her up and down, how she’s somehow holding herself up with nothing but the strength of her legs, and swallows hard.

His legs definitely  _ cannot _ do that.

He glances over at Dean, who’s apparently got the same mindset: his face is pale, and he looks more nervous than Cas has ever seen him. Dean grips the silk harder and Cas can just barely read his lips as he mutters, “Jesus Christ.”

“It’s not that bad,” Lisa says, untangling herself from the silk and returning right-side-up in a matter of seconds. “Three steps. Lean back, lace your legs, and let go. Trust the silk, it’ll hold you.” She starts making her way around the small studio, taking a few minutes with each person who seemed to be struggling, and correcting the form of those who are clearly acrobats in their spare time.

Cas rubs his hands on his thighs, surprised at how sweaty they’d suddenly become, before gripping his silk tighter than before. He exhales and leans back, straightening his elbows and craning his neck as he slowly wraps his legs around the silk. That part’s easier than he’d expected, but now he can’t seem to bring himself to let go.

“Trust it,” he breathes, loud enough for no one to hear it but himself. “Trust it, trust it, trust it.” For a few seconds, he wonders if he should let go quickly and get it over with, like ripping off a Band-Aid, or let himself take his time.

He sucks in a breath, closes his eyes, and goes with the first option.

His legs go taut, but instead of feeling the crush of his head against the yoga mat, Cas doesn’t feel anything. He glances below him; his head is a few inches off the ground, and he feels a swell of pride.

“Good, Cas!” he hears Lisa say from the back of the room. “Flip your hands over. Backs of palms against the floor.”

Cas makes the adjustment quickly, and even lets his legs go a bit looser. He cranes his neck to look around him, and glances up to see Dean still struggling. He swears under his breath, his limbs stiff and awkward as he tries to contort them one at a time instead of all at once. He fails again, almost losing his balance and toppling out of the silk, and turns his head sharply in Cas’ direction when a laugh escapes his lips. Dean’s green eyes look Cas up and down, and even though Cas knows his boyfriend is trying to seem pissed, he also can tell when he’s being checked out.

Finally, Dean grumbles, “Nobody likes a showoff, Cas,” and Cas laughs again.

Lisa makes her way over to Dean and rests her hand on his back. “Let’s restart this,” she says, and proceeds to coach Dean into the positions he needs to hit to end up like the rest of the class. Feeling like some kind of weird voyeuristic bat, Cas watches as Dean contorts himself based on the directions of Lisa’s hands. Moves his hands higher, curls his toes a bit more, pushes himself further back into the silk. 

Dean worries the corner of his bottom lip between his teeth as he tries to concentrate, and Cas is struck by how willing Dean is to try something he’s clearly never done, to make a fool of himself, to be the last one to get a move, all to spend time with Cas.

Cas’ heart swells with gratitude as well as pride when Lisa slowly moves her hands away, letting Dean swing down freely himself. He’s got his eyes closed, face scrunched up tight, but after a few seconds, he cracks open one eye, then the other, and looks around. Cas can’t help but smile when Dean’s face brightens as he realizes that he pulled it off. He looks around excitedly, his newfound energy betraying the otherwise peaceful nature of the class, and beams proudly at Cas.

“Fuck, yeah,” he mouths, and lifts his hands off the ground, straightening his arms and spreading his hands wide in triumph. Being careful to keep his balance, Cas is about to give Dean a quick thumbs up when he notices that in addition to his arms going straight, Dean’s legs did, too, their ability to hold him up along with them.

“Dean—” he starts, but a second after he gets the word out, Dean collapses onto the floor in a heap. Cas cringes as Dean stares up at the ceiling and their classmates gasp. Lisa hops out of her silk and is heading Dean’s way to make sure he’s okay, but he waves her off, still lying on his back.

“I’ll meet you at the bar next door after class, Cas.”

* * *

 

Surprising no one, Cas isn’t one for after-hours parties—or even ones that take a good chunk out of the work day. So when he adds his name to the RSVP list in the kitchen for the company Christmas party the next morning, there’s no escaping the peppering of questions and exclamations from his coworkers.

“Oh, shit,” Billie says, watching as Cas adds a quick “+1” to his name, and she grins at him. “Novak’s gettin’ serious with someone?”

Cas purses his lips and tries to hide his smile, but after a few seconds, he gives up. “I hope so.”

 

The night of the party, Cas walks into his room to find Dean standing in front of the full-length mirror, studying himself uncertainly. He’s changed into a new outfit Cas helped him pick out, and his head is tilted to the side, lips pursed in thought.

Almost unconsciously, Cas steps up behind Dean and snakes his arms around his hips, resting his chin on Dean’s shoulder. He watches in the mirror as Dean glances at him and smirks before brushing his lips against Cas’ temple.

“Hey.”

“What’re you thinking about?”

Cas is surprised by how quickly the answer comes. “How fucking awkward I look.”

Cas steps back at that, taking in Dean’s full form. His outfit—dark, well-fitting jeans, a gray button-down shirt, and skinny tie—is a bit out of his comfort zone, sure, but it’s not awkward by any means. Cas thinks he looks perfect, and tells him such.

Dean brushes it off. “You’re supposed to say that.”

“I don’t have to say anything.”

Dean looks down at his shoes, then at Cas through the reflection in the mirror. “Ever hear of imposter syndrome?”

Cas rolls his eyes. “People don’t get that for parties.”

“Then I’ll be the first.” Dean shrugs his shoulders once, then a few more times in an attempt to loosen up. “Trendsetter.”

“Hey.” Dean looks at him in the mirror again, and once they make eye contact, Cas turns him around so there isn’t a pane of glass between them. “You,” he says, resting his hands on Dean’s cheeks, then shoulders, then hips, “look gorgeous. Do you know how Balthazar described you when he first saw you?”

Dean wrinkles his nose. “Have I even met—”

Cas’ cheeks heat up at the realization that no, they hadn’t. “I might’ve shown him your photo on the Yuk-Yuk Hut website, it’s in the past,” he says hurriedly, and Dean barks out a surprised laugh. Before he can comment, Cas continues. “He said you were an adonis.”

Dean pauses, the comment clearly not what he had been expecting. “You say that like I should be surprised,” he finally says. He's trying to sound casual, but Cas doesn't miss the pleased tone of his voice.

“And he’s right,” Cas says. “In all the time we’ve known each other, never once have I thought,  _ boy, Dean should really try to make an effort _ , or  _ Dean’s looking a bit off today _ . And I guarantee,” Cas says, pulling Dean in close before pressing their lips together in a slow kiss that doesn’t last long enough, “no one at my job will think that, either.”

Cas is pleased when it seems like Dean agreed their kiss was too short: he gives Cas a crooked grin before leaning back in, resting his hands on Cas’ cheeks and kissing him back. As he starts to feel Dean’s tongue in his mouth, Cas begins to think that they don’t really  _ have _ to go to the party; he’d be perfectly fine staying right here for the rest of the night.

After a few more seconds, though, Dean pulls back, his eyes bright and betraying a fondness Cas has realized he tries too often to hide.

“All right, Romeo, let’s get a move on,” he says with a smile that makes Cas’ stomach flip. It’s the same look Dean’s given him almost every day since they started dating, but Cas doesn’t think his reaction to it will ever fade.

And he’s 100% okay with that.

 

If it was possible for the holiday sections from every big-box store in the tri-state area to hook up one drunken night, Cas is sure that the office is what their baby would look like. Every inch of space has been covered by paper snowflakes, cardboard Christmas trees and menorahs, Santa Claus cutouts, and other symbols of holiday cheer.

It should be fun, but all it does is make Cas feel claustrophobic and anxious.

The giant glass table usually reserved for important meetings is covered with bottles upon bottles of alcohol. Dean makes a beeline for the red Solo cups, fixes a drink for each of them, and hands Cas his cup before holding up his own. “To not fucking up my boyfriend’s work party,” he says.

Cas smiles and taps his cup against Dean’s. “To convincing my boyfriend he’ll do no such thing.”

Dean gives him an unimpressed look before downing his entire drink in one long swig. “Go on, then,” he says, sweeping his arm out lavishly. “Prove me wrong.”

The first hour or so is pretty straightforward, with Cas introducing Dean to each of his coworkers they come across. Billie peppers him with questions about comedy, improv theatres, storytelling shows, and who he thinks are the most underrated comics in the city. There are a few of his coworkers who, upon learning that Dean is a comedian, immediately start prompting him to tell them a joke or say something funny, something that Cas quickly learns makes Dean uncomfortable, but otherwise, the night is relatively uneventful.

Until Cas feels a hand drop heavily on his shoulder and looks up to see Zachariah standing next to him. 

His boss smiles humorlessly. “Glad you could make it this year, Novak.”

Cas plasters on a smile and nods, hoping his face isn’t betraying the way his stomach had dropped at Zachariah’s presence. “Wouldn’t miss it.”

Zachariah nods curtly, and it doesn’t take long for his eyes to wander toward Dean, and when they do, Cas is unnerved by the predatory gleam he finds there.

“I’m glad.” He glances at Cas, then adds, “Don’t be rude, Novak, introduce me to your guest.”

Cas’ eyes dart down to his cup. Before he can say anything, though, Dean notices Zachariah’s eyes on him, purses his lips, and sets his drink down on a nearby desk.

“You must be Zach,” he says, grabbing his hand in a firm shake. Cas can’t help but notice the twinge of alcohol-induced unsteadiness in his voice, and cringes. “And I think I owe you a thank you.”

“Do you, now?” Cas’ eyes widen as the side of Zachariah’s mouth quirks up in a curious, amused smile. “And why might that be?” 

“Dean, we should—”

“Well, accordin’ to Cas, you were the one who told him to interview a comedian, and lucky enough, he just happened to pick me. So in a way, I got you to thank for getting us together.”

The idea of Zachariah playing matchmaker makes Cas want to be sick, but when he notices the way Zachariah’s eyes narrow, unamused, and Dean’s eyes sparkle mischievously, he realizes that Dean knows exactly what he’s doing.

“I’m glad I could be of assistance,” Zachariah says through gritted teeth, and Cas looks down at his drink with a smile.

“Yeah, he’s great,” Dean says. “Don’t know what I’d do without him, honestly. Best person I know, and, between you and me—” he leans in, glancing around conspiratorially, “—guy’s hot as fuck.”

Cas chokes on his drink.

“Dean,” he manages to sputter between coughs, “we really should go.”

“And the best thing about Cas,” Dean continues, grabbing his wine glass, “is that when he eyefucks me, he’s at least subtle about it.”

Zachariah’s face has gone a perfect shade of crimson, and Cas can feel the heat from his glare on him. He can’t look his boss in the eyes, just mutters a quick apology under his breath as he grabs Dean’s hand and pulls him away.

“You’re going to get me  _ fired _ ,” he hisses. 

Dean waves him off and gives him a smirk. “You’ll be fine.”

Cas isn’t sure what it is that makes it clear he’s not convinced—his posture, his paleness, his wide eyes—but Dean catches on and grabs his hand. “Let’s get outta here.”

 

A few hours later, Cas stumbles into his bed after Dean, his stomach full of dollar pizza and a warmth that he’s not sure is from booze or the man next to him. He looks up at the ceiling, not wanting to be the first one to make eye contact, and startles a little when he feels Dean’s hand on his chest. He palms around for a few seconds before landing on Cas’ hand, then grabs it with a contented sigh.

“You,” Dean says, tilting his head slightly and smiling at Cas, “are good.”

Cas smiles. “You are, too.”

“That’s not the best thing about you, by the way,” Dean adds suddenly.

Cas furrows his brows. “What?”

“When I told your boss the best thing about you,” he says. “I can tell you more if you want. There’s a lot.”

Cas opens his mouth to reply, but just looks at Dean instead, at the earnestness and vulnerability in his slightly too-drunk eyes, and smiles. “I believe you. Thank you, Dean.”

Dean grins at him before scooting closer and wrapping his arm around Cas’ waist and hooking his chin over his shoulder. “‘S nice,” Dean slurs. “To have someone who gives a shit.” Cas smiles down at his pillow like a smitten middle schooler and plants one more kiss on Dean’s cheek.


	5. Chapter 5

When Cas wakes up in an empty bed, he wonders briefly if last night had been a dream, that Dean hadn’t gone with him to the Christmas party, that he’d chosen an open mic instead. For a quick second, Cas’ heart sinks at the thought, and he’s resigned to disappointment as he gets out of bed until he catches a glimpse of Dean’s boots, jeans, and sweater from last night piled in the corner.

One side of his mouth quirks up with a smile.

As Cas heads down the hallway toward the kitchen, Balthazar appears and grins broadly, smacking him on the shoulder. “You did good, Cassie.”

“I — ”

“ _ He _ ,” Balthazar says, gesturing toward the kitchen with his head, “is a specimen, indeed. And just enough of a dick to dish it out, but also take it. Very important, if you ask me.”

Cas doesn’t know why, but he feels an odd sense of pride at Balthazar’s approval. Balthazar smirks. “Well, aren’t you just a goddamn smitten kitten,” he says. “Go on, Cassie. Your husband awaits.”

This time, it’s Cas’ turn to smack him, but Balthazar just laughs and heads toward his room.

Dean is sitting at the tiny kitchen table, stacks of papers scattered around him, as well as several sheets of holiday-themed stickers. A tattered gradebook is open at his right hand, and as he meticulously checks the work, he pulls out the pen that’s clenched between his teeth and records more info in the book.

“Dean?” Cas asks, rubbing the heel of his palm against his eye to try and rid himself of tiredness. 

Dean looks up at him, a little surprised. “Oh. Hey,” he says apologetically, gesturing toward the mess on the table. “I just gotta get these done before the kids leave for break, they were in my bag and you were still asleep and — ”

Cas doesn’t realize he’s making a face until Dean’s scrunches up in confusion. 

“What?” Dean asks, his eyebrows furrowing together at Cas’ outlandish reaction. When Cas doesn't reply right away, Dean starts looking around. “What, Cas?”

“You wear  _ glasses _ ,” Cas says, trying and failing to hide the delight in his voice. “Oh, my god.”

Dean’s eyes widen behind the thick frames, and his cheeks go pink before he looks back down at his work. “Only for reading,” he mumbles, quickly pulling them off his face and dropping them onto his gradebook.

“Why didn’t you tell me? How long have you had them?” Cas pulls up a chair next to Dean, beaming. His thing for guys in glasses is  _ insane _ , and knowing that Dean wears them puts him one step closer to a perfect specimen in Cas Novak’s book, shitty eyesight be damned.

Dean still won’t answer, or even look at him. Instead, he tries to resume focusing on his work, but Cas can tell something’s wrong.

“Wait, are you embarrassed?”

“Why do you think you've never seen ‘em before?”

_ Jesus _ . Cas knows kids tend to be embarrassed when they get glasses for the first time, but Dean is a grown man. “Why would you be embarrassed over something that helps you see? Something that you  _ need _ ?”

Dean is silent for a few seconds. “They used to break,” he says. “Or they would get broken. Or stolen. At school. A lot.”

The fractured sentences provide all the answer Cas needs, even though he can't reconcile his snarky, confident boyfriend with someone who'd be picked on in school, or at any point in his life, really.

“You're amazing with them,” he says, gently easing the arms over Dean's ears and resting the glasses on the bridge of his nose, “and you're amazing without them.” He lifts the glasses up onto the top of Dean's head. Dean isn't looking at him, but Cas can still see the way his lips are starting to quirk upward. “I've always liked a man in specs, though,” he finishes.

“Goddamn, Cas,” Dean says. “If I’d known they’d be such an aphrodisiac, I’d’ve pulled ‘em out ages ago.”

“Good word,” Cas mumbles against Dean’s lips. “Looks like we need to make up for lost time.”

Cas can feel Dean’s lips smile against his own, and tugs the frames down over Dean’s eyes again before kissing him harder.

Time seems to stop while he and Dean are together, and Cas can’t think of anywhere else he’d rather be. Dean’s fingers tangled in his hair, tongue sliding into his mouth, chest pressed to his — he almost doesn’t hear the clatter of bowls and utensils.

He peeks up over Dean’s shoulder and sees Balthazar standing at the breakfast bar, looking bored out of his mind and pouring some cereal into a bowl. Dean is insistent, nipping at his lip to get Cas’ attention back to him, but when Cas doesn’t react, he turns around, too.

Balthazar stands oblivious for a few seconds before realizing that all eyes are on him. “Carry on, gentlemen,” he says smoothly, waving a hand dismissively without looking up. “Don’t let me interrupt your romp.”

* * *

 

“Come on, don’t give me that.” Dean glances at Cas over his shoulder, balancing a pile of gifts in his arms. “You’ll be fine.”

“You’re not the one meeting your boyfriend’s family for the first time,” Cas says, nodding to their Uber driver before pocketing his phone, watching the tiny Prius speed away down the street. “It’s nerve-wracking.”

Dean rolls his eyes. “Sam might look like a sasquatch, but I promise, the only way he’d hurt you is by hugging you too hard.”

Cas’ face goes pale at that, and Dean jerks his head toward the brownstone in front of them. “He’s a teddy bear, and Eileen’s a sweetheart. Plus, she might even teach you how to swear in sign language.”

“Has she taught you?” 

Dean shakes his head solemnly. “Haven’t been able to convince her yet.” He waggles his eyebrows hopefully. “But maybe you will.”

“Somehow I doubt that.”

Dean rolls his eyes and awkwardly readjusts the gifts in his arms before heading toward Sam and Eileen’s place. Cas almost trips over a book sealed in a plastic bag sitting on the stoop, and glances back at it questioningly. His curiosity is quelled by the biting cold outside, sharply contrasted by the warmth that bursts out onto the steps when Sam opens the door to their apartment.

“Hey, guys!” he says excitedly. He steps outside and all but wrenches the gifts from Dean’s arms before enveloping him in a giant hug.

“Good to see you, too, Sammy,” Dean says, trying his best to pat his brother on the back while his arms are pinned to his sides. He glances back over his shoulder and shoots Cas a  _ See? Told you _ look.

“We’ve been cooking for hours,” Sam says, wrapping his arm around the slim brunette that appears in the doorway next to him. Their height difference is so pronounced, they almost look like Russian nesting dolls waiting to be stacked, and Cas huffs out a quick, quiet laugh at the thought. Sam turns his attention to Cas, eyes warm and bright. “You must be Cas,” he says, and in a matter of seconds, Cas finds himself in a hug of his own.

Dean nudges his way inside and gives Eileen a hug and a quick kiss on the cheek. “Don’t strangle the guy before he gets in the door, Jesus.”

Sam ignores Dean and grins down at Cas before running a hand through his hair. “I’m Sam,” he says, “and this is my girlfriend, Eileen.”

Eileen smiles and gives him a hug, too, one that’s much softer than Sam’s. “Nice to meet you,” she says, signing words as she speaks. “You should’ve seen Sam when he heard that Dean wanted to bring someone.”

Cas raises his eyebrows. “Oh?”

“Dean  _ never _ brings anyone except comics,” Sam says, “and they’re nice enough, but I don’t need 80 different jokes about why my food sucks.”

“It’s because  _ I’m _ the chef in the family,” Dean says matter-of-factly.

“Whatever helps you sleep at night, dude.” Sam rolls his eyes and takes a few steps back into the apartment, stumbling over a stray gift in the process and almost losing his footing.

“Diggin’ into the Christmas cheer a little early, Sam?” Dean asks, chuckling when Sam flips him off.

“Oh, excuse me for being excited about meeting the first guy you’ve brought home in ages,” Sam retorts, grinning at the way Dean’s cheeks color under his freckles.

“Uh, someone dropped a book outside,” Cas says, gesturing behind him in an attempt to change the subject. “I can go grab — ”

“Oh, no, it’s the stoop exchange!” Sam says, grinning. “Someone’ll take it, then leave us a book, and we’ll pass it on to someone else. Community reading.”

Cas smiles at how endearing he finds the idea (and Sam and Eileen, for that matter), but Dean scoffs. “You’re such a fucking hipster, Sammy,” he says, peeling off his boots and dropping his coat to the floor. “Now c’mon, stop embarrassing yourself and let’s get this party started.”

Cas normally doesn’t like admitting when he’s wrong, but for the first time in recent memory, he’s glad to be. Sam and Eileen are welcoming and funny, and such a contrast from most of Cas’ own family that he’s almost shell-shocked.

He adds it to the list of things he could definitely get used to.

After dinner and presents — during which Eileen gave Dean a copy of a book called  _ Super Smutty Sign Language _ , much to Dean’s delight — they lounge around in the living room, the small Christmas tree twinkling in the corner.

“Has he started including you in his bits?” Sam asks through a mouthful of cookies.

“No,” Cas says hesitantly, not having realized that would even be a possibility.

“Good. Make sure he doesn’t,” Sam says, looking pointedly at Dean, who takes a long swig of his beer before setting his bottle down on the back of the couch. “Nothing’s off limits if your brother’s a comedian. Give him parameters, because I’m sure it’s even worse if you have one for a boyfriend.”

Dean rolls his eyes. “Come on, Sam, you  _ know _ that joke was fucking gold.”

“Sure, which is why Crowley still hasn’t come calling for you to be on his show yet.”

Dean seems stung by Sam’s comment, and Cas wrinkles his nose at the reaction. Fergus Crowley, the snarky, arrogant late-night TV host, seems like he’d be as much fun to be around as a pack of rabid dogs, but for some reason, Dean seems to be disappointed he hasn’t had the chance yet.

“Fuck off, Sam.” Cas can tell that Dean is trying to sound good-natured about it, but the tightness in his voice and the way his jaw locks in place gives away the fact that Sam had touched a nerve.

As they’re getting ready to leave, Sam and Dean still bickering and jostling with each other, Eileen taps Cas on the elbow. 

“I hope you had fun,” she says.

“I did, thank you. Everything was wonderful.”

“Dean really likes you,” she says. “I can tell.”

Cas isn’t sure what she’s expecting from him at this point, and tries to think up something decent to say while he buttons up his coat. “Well, that’s good to know,” he says, and he isn’t sure if it’s the wine or just brazen confidence that makes him add, “because I like him, too.”

She smiles, her eyes sparkling in the warm light of the apartment hallway. “Welcome to the family,” she says, and makes circles with the thumbs and index fingers of both hands. She turns her wrists so that the backs of her hands are facing Cas now, and repeats the motion a few more times, mouthing  _ family _ as she does so.

“Family,” Cas repeats, keeping his eyes on her hands as he mimics the sign. He looks up at her with a smile when he’s committed the sign to memory, then does it on his own. “Family. Thank you.”

“And in case you need it,” Eileen adds. She holds up her pinkie, index finger, and thumb, letting her middle and ring fingers curl into her palm.

“What’s that?” Cas asks, recreating the sign with his own hand.

“‘I love you.’”

* * *

 

Christmastime should be relaxing.

It should be a time to sleep in, to watch the snow blanket the city whenever they’re lucky enough to have some, to pad around the apartment in socked feet and watch cheesy action movies all day.

It should be a lot of things, but Cas knows for sure that one thing it  _ shouldn’t _ be is full of comedy shows no one even goes to. 

That doesn’t stop Dean, though. He’s trudging through the snow and slush almost every night, performing for handfuls of people who have no interest in comedy, but needed a place to duck into away from the cold. Cas had gone to the last couple open mics, trying and failing to laugh and get others to clap, to no avail. Eventually, Dean tells him he doesn’t need to come, claiming that he doesn’t want him to hear too many of his jokes before they’re ready.

Dean is running himself into the ground, going from open mic to open mic with barely enough time to grab a hot dog or falafel for dinner before heading to  _ yet another _ open mic, stopping by his apartment for a quick blowjob or fuck while Balthazar’s out, and crashing for a few hours to try and fix his sleep schedule before school starts up again. Cas is exhausted just watching him, but no matter how much he tries to convince him otherwise, Dean insists that he’s fine, that it’s all part of the grind, and he’ll be able to have a normal schedule eventually, once he’s paid his dues.

Cas decides to let Dean think he believes him.

  
  


When Dean calls Cas in the middle of the work a few days after break ends, he assumes the worst. He scoops up his still ringing phone and makes a beeline for the break room, pressing the phone up to his ear.

“Dean, is everything okay?” He’s half-expecting to hear Sam on the other line, telling him that Dean’s in the hospital after collapsing from exhaustion, so he sighs in relief when Dean’s gravely voice comes through.

“Yeah,” Dean says, sounding almost breathless. “Yeah, everything’s great.”

Cas furrows his brows at the unexpected response. “I didn’t think you’d call in the middle of work unless it was an emergency.”

“They’re at recess.” Dean clears his throat, and Cas pictures him scrubbing a hand down over his mouth before he says, “Cas, I got booked on Harvelle.”

And it takes all Cas has for him not to drop the phone.  _ Late Night with Jo Harvelle _ is one of the most hallowed names in late-night comedy; it’s one step away from  _ The Tonight Show _ .

And Dean is going to be on it.

“Dean, that’s incredible!” Cas says, relief and excitement replacing the dread that had been pressing down on his chest. “What’d everyone say?”

Dean pauses on the other end of the line, and for a second, Cas wonders if they got disconnected.

“Dean?”

“I, uh, I haven’t told them yet.” His voice is sheepish, and Cas is about to ask why not when it suddenly hits him like a punch to the face.

“Am I the first one you told?” he asks softly.

Dean chuckles awkwardly. “Guess so. They just called during lunch,” he continues. “Apparently there was a scout at the Yuk-Yuk show on Tuesday. Harvelle’s original guest bailed, and they need a replacement. Quick and dirty.”

Cas leans back in his chair, pressing a hand over his mouth to try and contain the smile spreading across his face. “I’m so proud of you, Dean.”

“Thanks, Cas.” A sudden chorus of voices comes from Dean’s end of the phone, and Cas can hear him cover the phone with his palm before calling, “Hey, no running! Uh, I’ll see you later. Dinner tonight?”

“Of course.” Cas hangs up just as he hears a little girl shout, “Mister  _ Win _ chester, Davey broke — ”

Cas looks down at the phone in his hand and smiles up at the ceiling. If this goes well, it could pay off all the dues Dean keeps talking about. He and Cas could go out to dinner and spend the night together like normal couples, without him running off or coming in ridiculously late. This is it. This is the break Dean has been waiting for.

The break  _ they’ve _ been waiting for.

On his way back to his desk, Cas types out a quick text message.

_ Cas, 1:02pm: Congratulations, Dean. I’m so, so proud of you. _


	6. Chapter 6

Call him crazy, but Cas had been expecting the green room to be, well,  _ green _ .

Instead, he, Sam, and Eileen are sitting on a couch situated in front of a coffee table stocked with snacks, water, and beer while Dean paces and cracks his knuckles.

“Dean, relax,” Sam says, taking a bite of an apple before leaning back in his seat. “You’ll do fine.”

“People are  _ supposed  _ to laugh at you,” Eileen adds, grinning, “so even if you mess up, you won’t be able to tell either way.”

Dean flips her off, eyes narrow, and she returns the gesture. Sam glances at Cas and rolls his eyes. Cas smiles quickly before getting up and stopping Dean mid-stride.

He’s been doing this for days, ever since he got the call. “You’re fine,” Cas tells him, gripping his shoulders and forcing Dean to look him in the eyes. “You’re good at this. You  _ love _ this. They picked you for a reason, Dean.”

“Yeah, for a pity party,” Dean mutters. Suddenly, something small and brown — a cashew, Cas realizes — smacks against Dean’s temple. Dean’s hand flies to his head and he glares at Sam, flipping him off with his free hand. “What the fuck was that for?”

“For being an idiot,” Sam says simply. He takes another cashew and pops it into his mouth, then leans back on the couch, slinging his arm over Eileen’s shoulders.

“Fuck you, I’d like to see how  _ you _ handle getting ready to try and make hundreds of thousands of people laugh,” Dean shoots back. Sam launches into a retort, and Eileen couldn’t be less interested, slouching down the couch and tilting her head back to face the ceiling, eyes closed.

While he tries to tune out the brothers’ arguing, Cas notices a piece of folded yellow construction paper on the table. He brushes aside the few food wrappers and other papers covering it and picks it up.

_ Good luck Mr. Winchester!!! _ is scrawled across the front of the card in five different colors of crayon, and almost as many kinds of children’s handwriting. Cas opens the card and is greeted by a drawing of a stick figure standing in front of a microphone, a giant spotlight beaming down from the top of the card. Surrounding the figure are the signatures of Dean’s students, at least twenty of them, backwards letters and all.

Cas grins down at the card, absently running his thumb over a few of the names, then looks up to see Dean watching him. His eyes dart down to the card, a hint of a smile playing on his lips, and Cas closes it gently. He sets the card back on the table, strategically behind the fruit bowl and water bottles so that Sam and Eileen don’t notice and pepper Dean with questions, and taps it with two fingers.

Before Dean can say anything, a PA knocks on the door and sticks her head into the room. “Show’s starting in five,” she says, gesturing for Sam, Eileen, and Cas to follow her out into the studio to take their seats.

They get to their feet and start following the PA out to the stage. When he passes Dean, Cas grabs his hand and brushes his lips against his knuckles. “You can do this,” he breathes, giving Dean’s hand a quick squeeze before leaving the room.

He glances back over his shoulder, and the last thing he sees before the door closes behind him is Dean looking down at the hand he’d just kissed.

  
  


_ Late Night with Jo Harvelle _ is only an hour-long show, but it seems to drag on for ages as Cas waits for Dean’s performance. He’s got to resist the urge to check his phone as monologues are delivered, bits are played out, and jokes are made; finally, Jo’s waiting for the sign from her producer that they’re back from commercial, and Cas takes a deep breath.

He doesn’t miss the way Sam grabs Eileen’s hand, either.

“Our next guest is making waves in the local comedy scene,” Jo says, leaning back in her chair and kicking her feet up on her desk, crossing them at the ankles. “So who knows, maybe you’ll see him on Crowley sometime. But we found him first, and I’ll tell you right now, the guy’s  _ really _ fucking good. Give it up for New York City’s own Dean Winchester!”

The producer rolls his eyes and scribbles down the time where Jo swore so that it can be bleeped out later, then gestures for the camera to swoop toward Dean, who’s entering stage right. He heads for his mark, waving quickly at the audience as they clap and cheer.

When he finally looks up, he seems confident enough, but Cas can see the nervousness in his eyes; he sucks in a breath through his teeth and waits.

_ Come on, Dean. _

“Thanks for having me,” Dean says. “It’s, uh — ” He’s cut off by a sudden burst of feedback, and the audience cringes as Dean holds the microphone away from him, staring at it like it’s a snake with two heads.

Cas just barely hears Sam mutter, “ _ Shit _ ,” under his breath.

“Well, now that you’re all awake,” Dean continues hesitantly, “you, uh, you wanna hear who has the most ridiculous phrases out there?”

The audience claps and whoops, still on his side. Even though Cas knows they’re throwing Dean a bone, he still feels a small sense of calm at their mercy. Cas doesn’t know much about comedy, but one thing he knows for sure: static that loud in a club and Dean would’ve been eaten alive.

“Us, apparently.”

Cas’ heart clenches as someone boos, but Dean laughs and points up at them. “I agree, man! But honestly, y’all know the phrase  _ eat shit _ ?”

The producer is adding yet another note as the audience cheers in recognition. “It’s one of my favorites,” Dean continues, “but I said it in front of one of my friends the other day, and she looked at me like I’d just told her  _ Days of Our Lives _ is my favorite TV show. She had no idea — no  _ idea _ — that phrase existed, and she thought I legitimately left my apartment one day, came upon some dog shit, and just had myself a nice meal.

“And even if I  _ did _ do that, it’s my business.”

The audience laughs, and Dean grins, relaxing into his element almost immediately. Cas watches as he continues his jokes, getting more and more animated the more comfortable he becomes, and it takes all he has not to run up on stage and give Dean a giant hug.

After what only seems like a few seconds, Dean raises his hand, brighter and more confident than when he walked out. “I’m Dean Winchester, thanks, y’all, have a good night.”

Dean looks out at the crowd, breathing like he’s just gotten off a roller coaster. Everyone claps and cheers, and he beams. When his eyes land on Cas, though, they soften immediately, and he winks, just like he did the night they met.

Without thinking about it, the fingers of Cas’ right hand form into one of the signs Eileen had taught him a few months back, and he holds it in front of his chest so Dean can see. Dean squints at Cas’ hand, and Cas can tell exactly when he realizes what the sign is. His eyes dart down to his own hand, and he quickly flicks his wrist up and mirrors the same sign back to him.

  
  


After Harvelle, Dean starts landing earlier gigs. Instead of going on at one or two in the morning in front of a handful of drunks and half-asleep comedy nerds, he’s performing at eight for tourists and, sometimes, even people who seek him out specifically. They buy tickets with his name printed on them. Cas is one of those people: he has one of Dean’s first headliner tickets in a small frame on his nightstand, next to a photo of the two of them.

It’s exciting, and Cas knows he should be thrilled, but instead of spending more time with Dean like he had been promised, Cas finds himself seeing his boyfriend less and less. Fellow comics are constantly asking him to go out for drinks after sets, and more often than not, Cas will be the one encouraging Dean to go, that they can hang out afterwards, that it’ll be fine.

Dean seems to think this is true — now, Cas just needs to convince himself of the same thing.

 

* * *

 

They’re walking around the Strand when Cas sees them. Two girls, probably in their late teens, glancing not-so-subtly their way and whispering to each other. Dean is oblivious, engrossed in deciding between two variant covers. Cas is half-tempted to drag Dean away before he notices, but he knows the girls would more than likely follow him; better to just get it over with.

All he had wanted was an afternoon out with his boyfriend, sharing one of his favorite places with him. That fantasy seems to be out of the question now; he grabs a copy of the nearest book and tries not to overact when the inevitable question comes.

“Cas, which one do you — ”

“Excuse me, are you Dean Winchester?”

Dean looks up, a bit confused, but quickly smiles at them. Cas hates how goddamn adorable it is that Dean still hasn’t processed the fact that people know who he is. “Sure am.”

“Oh my god, you were  _ so good _ on Harvelle the other night,” one of the girls says. “We were dying.”

Dean chuckles. “Well, dying’s not good. Appreciate the sentiment, though.” Cas knows he shouldn’t be so jealous when Dean winks at them, but he is.

“Can we get a picture with you?” one girl says, holding her phone out hopefully.

“‘Course, sweetheart,” Dean says, motioning for them to stand with him.

“Great!” The girl shoves her phone at Cas without looking at him, and Cas fumbles the phone before pointing it at Dean and the girls. He snakes his arms around both of their waists, his trademark crooked grin in place, and Cas’ stomach clenches as he snaps the photo.

“I took a few,” he says stiffly, handing the phone back to the girl. She gives him a smile before turning back to Dean.

“Thank you so much! I hope we see you on TV again soon.”

Dean gives her a quick wave. “You and me both.”

The girls leave, and Cas takes a deep breath through his nose, trying to ground himself through the anxiety that’s suddenly taken over. He feels Dean’s fingers entwine with his and squeeze quickly.

“You all right?” Dean asks when Cas opens his eyes. Cas breathes in once more before looking up at his boyfriend and plastering on a tight smile. “Sure.”

Dean’s face falls. “You’re not all right.” He looks down at the two books and returns them to their shelves before grabbing Cas’ hand. “Come on.”

  
  


“I’m not the most well-versed in relationships,” Cas says in the coffee shop, studying his drink. “But out of the few I have had, I’ve never had to share my partner with anyone else.”

Dean blinks, clearly trying to sort out his thoughts. “You got news for me, Cas?” he asks. “You’re not sharing me with anyone.”

Cas shakes his head. “No, not really, but that — ” he gestures vaguely toward the Strand across the street, “ — doesn’t happen to regular couples.”

Dean considers this and nods to himself. “Touché,” he says. “Listen, Cas, this is all new to me, too, okay? It’s still fucking weird that people outside of the Yuk-Yuk Hut even know my name.”

“I know.” Cas wrings his hands in his lap, then looks back up at his boyfriend. “I’m sorry. I’m ruining this for you. You should be excited, everything is finally falling into place.”

Dean barks out a disbelieving laugh and shakes his head. “Cas, you’re the best fucking thing that’s happened to me. Better than Harvelle, better than fans, better than anything. And I’ll make sure you know that.”

He reaches across the table and takes Cas’ hand in his, tugging him forward until he’s close enough to drop a quick kiss on his lips. “We’re in this together,” he says. “Promise.”

Cas smiles softly and squeezes Dean’s hand. “Promise.”

* * *

 

They’re just about to leave Dean’s apartment for the movies when Dean’s phone rings. He pulls it out of his pocket and rolls his eyes at Cas, but accepts the call anyway. “Hey, Benny, what’s up?”

Dean pauses, listening to the voice on the other end of the line, and Cas notices the way his eyes brighten at whatever he’s being told. “Really? Dude, of c — ” That light disappears just as quickly as it showed up, though, as Dean corrects himself. “Does it have to be tonight? I can’t — yeah, I know it’s booked, but — ”

Cas smacks at Dean’s arm, and Dean glances at him. “Hold on. What?” he says, holding his phone upside down and away from his face. 

“What’s going on?”

“Nothing.”

Cas gives him an impatient glare, and Dean sighs. “It’s just this show, I’ve been trying to get on it for months. It’s tough to get a monologist gig, and — ”

“Tell them you’ll do it.” Cas has no idea what a monologist is, but if it’s important to Dean, it’s important to him, too.

Dean’s brows furrow together at that. “Cas, I — ”

“Tell them you’ll do it,” Cas repeats.

Dean pauses, and for a second, Cas thinks he’s actually going to say yes. He starts to bring his phone back to his ear, but then he shakes his head at the last second. “No, man. We had a date.”

“I’ll go with you. I can come see you perform, and then we can go get dinner afterward. Still a date, just a different one.” Cas leans forward and catches Dean’s face in his hands, gently tilting his head up to look at him. “It’s okay,” he says. “I promise.”

Dean keeps his eyes averted for a few seconds before finally deciding to look at Cas. He gives him a small, crooked grin that makes warmth flood in Cas’ chest, says, “Thanks,” and leans forward, pressing their lips together in a quick kiss before turning back to the phone. “Benny? Hey, if you can get me a comp ticket, I’m in.”

 

“So what is this?” Cas asks as they walk up the steps of 23rd Street station. 

“A comedy show,” Dean says, as if it’s the most obvious thing in the world.

“I figured.” Cas rolls his eyes and nudges Dean. “But what kind of show? Are you performing?”

Dean shrugs one shoulder. “Sort of. I’m gonna be a monologist, which basically means that I’ll...run the show, in a way. It’s improv, so someone in the audience is gonna give us a word, and I’ll think of a story from my life that has to do with the word, then everyone else will act it out. Make sense?”

“Vaguely.”

Dean chuckles. “Good enough.”

 

The show is back at the Laugh Factory, where Cas and Dean had their first date —or interview; tomato, tomahto—and in the spirit of the memory, Cas makes a beeline toward the table they sat at that night. Two women in their early twenties are already sitting there, but when Cas gestures to one of the empty seats, they nod.

He looks down at the familiar etchings, and spots one that looks fresher than the rest. Instead of regular initials, two names have been strategically carved into the wood around the other initials and hearts. They’re small and scratchy, but when Cas finally is able to read them, his heart about stops.

_ Dean + Cas _

Cas suddenly recognizes Dean’s scrawling handwriting, distinct even in the wood, and after tracing his fingers along the words, rests his entire palm on them. He smiles up at the ceiling, heart full. He doesn’t know how long the words have been there, but just the fact that Dean cared enough to do it in the first place dissolves all his worries and anxiety over the past few weeks. When he looks back down at the etchings, he notices the way the couple’s hands are tangled together on the tabletop, and resumes his favorite pastime, all optimism and butterflies and positivity. 

_ This is their first date, so they’re trying to impress each other. They met at one of these shows, after having been in the same improvisation...troupe? Class? Class. She had asked her out as part of a scene, and had to clarify afterward that the invitation was real. _

_ It’s cute. They’re cute. The one with the hat refuses to go home as long as she can help it because her parents won’t stand for the idea of her having a girlfriend. She’s nervous to get into that part of her life with this girl, but figures it will come with time. They’ll _ —

Cas’ thoughts are interrupted when a bubbly, overly excited woman bounds up to the stage and starts tapping the mic in her hand. “Hello!” she says, waving frantically out at the crowd. “Hello, hello! I’m Becky Rosen, and I’m  _ so _ glad you all could make it out tonight for our show!”

The crowd cheers, and Cas claps.

“We’re going to have a great show tonight, so let’s get right to it. Meet our improvisers: Chuck Shurley, Rufus Turner, Hael Jacobson, and Pam Barnes!”

The claps and whoops continue, and for a second, Cas wonders if he’d somehow made a wrong turn into a different show. He cranes his neck to look at the stage, but there’s no sign of Dean as the improvisers jog out onto the stage.

“Now, for anyone who’s never been to one of these shows, the rules are simple. We’ll ask you for a word, our monologist will tell us a story from their life based on that word, and our improvisers will act it out and make it even better. Got it?” More cheers. “And now for our monologist, fresh off his spot on  Harvelle , Dean Winchester!”

Dean bounds out onto the stage, all smiles and energy, and Cas immediately knows that they made the right decision. He claps his hands a few times and waves as the cheering continues. Becky hands him the microphone, and he greets the crowd with a quick, “Hey, y’all, what’s my word gonna be?”

Cas hears a few — speedboat, convention, foreplay, exhaustion — but the one that Dean latches onto is “road trip.” 

“Road trip,” he says. “Road trip, road trip, road trip. My family, we  _ lived _ for road trips, mainly because we pretty much lived on the road…” He keeps going, regaling the crowd with stories of him, Sam, and their father crossing county lines and the different escapades he and Sam would get into at the motels they’d stay at while their dad worked.

The vagueness of his father’s job isn’t lost on Cas, but what he focuses on more was how goddamn  _ happy _ Dean looks, especially once the improvisers start bringing his story to life with their own twists. He cringes and laughs and claps along with the crowd, and it makes Cas smile.

Dean is laughing, smiling wide, when he makes eye contact with Cas during a scene, and when he does, his smile gets even bigger. A warm glow starts in Cas’ gut and rushes through his body as he realizes that he’s making Dean smile more than the thing he loves most in the world. 

This time, Cas is the one who winks first.

  
  


“I’m glad we did this,” Cas says after the show. “I’d never seen you do anything like that before.”

“What can I say,” Dean says with a smirk. “I’m a man of many talents.”

“You can say that again, Winchester.”

Cas turns around to see Rufus and the rest of the improvisers heading toward them. Dean turns around and, amidst a flurry of handshakes and back slaps, compliments their work, as well.

“You guys were great, holy shit.”

“Hoping this won’t be the last time we see you,” Pam says.

Dean grins. “Oh, I’ll be back. Don’t you worry.”

Pam nods approvingly. “We’re all heading out to grab some drinks; want to join?”

Dean hesitates as Cas’ eyes immediately avert down to the floor. “I, uh, actually — ”

“You should go.” Cas is surprised by his own voice; Dean studies him curiously.

“Cas, we had a date.”

“We did,” he says, nodding, still riding the high from discovering their names on the tabletop. “And it was great. We’ll have time for another one. Go.”

Dean keeps his eyes on him, searching for some kind of break in Cas’ armor. When he doesn’t find one, he grabs Cas and tilts his head back, giving him a deep kiss. “Thanks,” he breathes with a small smile. “Meet you at your place tonight?”

Cas nods again. “Have fun.”

Dean squeezes his elbow before heading off, and Cas makes his way toward the subway, trying not to dwell on the disappointment of his own decision.

 


	7. Chapter 7

When Cas rolls over after waking up in the middle of the night, he’s expecting to feel Dean’s warmth next to him. When he doesn’t, all traces of sleep disappear, and he straightens immediately, grabbing his phone. 

3:28am. No missed calls or texts; Dean should be here by now.

He shines his flashlight onto the other side of the bed — undisturbed, where Dean should be — and throws back the covers, heading out of his room and down the hall. He squints into the darkness, feeling his way down the hall toward the living room. He makes a mental note to buy a lamp for the hall as he stumbles through the dark apartment.

He’s about to flick on the light when he trips himself up over something on the floor. “ _ Shit _ ,” he hisses, hopping up on one foot and holding his bruised toes. In an impressive display of flexibility — the aerial yoga must be paying off, he decides — he turns on the light, and realizes that he didn’t trip over a some _ thing _ , but a some _ one _ .

Dean is sprawled out on the living room floor, boots strewn off to the side, jacket draped over the chair. His head looks like it came dangerously close to hitting the coffee table on his way down. Cas can smell the booze wafting off of him.

“Jesus, Dean,” he says softly. He gingerly sets his sore foot back on the ground before grabbing a blanket and draping it over Dean’s form. Almost like a reflex, Dean grabs a fistful of the blanket and tugs it up under his chin.

Defeatedly, Cas drops down onto the couch, wraps himself in another blanket, and tries to fall back to sleep with his unconscious boyfriend at his feet.

  
  


Dean is still on the floor when Cas wakes up the next morning. He looks down at him for a few seconds, and as he gets to his feet, decides to “accidentally” trip over Dean’s side.

“Wh’ _ fuck _ ,” Dean mumbles, rolling over onto his back with a groan. Cas ignores him and heads for the kitchen, making himself a cup of coffee. Dean only starts to stir when he smells the bagel Cas has begun toasting, and drags himself to his feet before practically collapsing into the chair and across from Cas, burying his face in his hands.

“Wanna turn the light off, huh?”

“Nice of you to stop by,” Cas says, his biting tone betraying the calm aura he had been trying so hard to keep. 

Dean squints at him. “What?”

“What time did you get back last night?”

“I don’t know, one?”

“I was up til two.”

Dean rolls his eyes and buries his face in his arms on the table. “Late, all right? I came in  _ late _ .”

“I woke up at 3:30 and you weren’t in bed.”

“I didn’t want to wake you up, Cas, Jesus,” Dean mutters, rubbing the heel of his hand against his eye.

“I tripped over you passed out on the fucking  _ floor _ !” Cas shouts, his voice getting louder than he had anticipated, and, if his expression is anything to go by, Dean had, either. Dean opens his mouth to respond but can’t think of anything, opting instead to grab his own mug of coffee and slouch back in his chair.

“I was worried,” Cas says quietly. “You weren’t here, and you were supposed to be, and I just — ”

“I’m fine.” Dean blinks owlishly and yawns. “Just lost track of time last night, that’s all. I’ll do better next time.”

Cas nods, but doesn’t say anything. They sit in an awkward silence for a few moments until Dean tries his hand at another conversation. “How’s your writing going?” The question doesn’t feel genuine, more like a balm being used in an attempt to clear the air, and Cas treats it as such.

“Fine.”

“That’s, uh, good,” Dean falters, clearly expecting some elaboration. “Want to work on it later today? I can work out a few jokes, you can get some good dialogue lines in, we’ll get a pizza.” He waggles his eyebrows, and no matter how hard he tries to fight it, Cas grins.

“That would be nice.”

 

Dean is on his best behavior the next few weeks in an attempt to redeem himself. He calls Cas almost every day, makes sure to let him know when he’ll be late, and even skips an open mic down at the Comedy Cellar to make it to a book reading Cas had been looking forward to.

Cas knows there’s no such thing as a perfect relationship, but the way Dean’s been acting lately makes him feel like they’re pretty damn close to it.

Which is why, an hour and a half into Cas’ birthday celebration — he hates referring to it as a party — Cas is having a hard time believing that Dean still hasn’t shown up.

Sure, he surprised him with a few things earlier that day, but he’d been the one to plan this party with Sam, just them and a few of their closest friends. Gabe even made it, and on the Yuk-Yuk Hut’s busiest night.

“I’m sure he’s just running late,” Sam says, sidling up to Cas at the bar. Almost two hours of small talk and questions about him and Dean have been enough to drive Cas to more than a few drinks, and he sighs.

“He planned this, didn’t he?”

Sam nods. “He’s gotta have a good reason. He wouldn’t just ditch this, especially not for you. I’ve seen the way he looks at you,” he adds with a grin. “Guy’s head over heels, man.”

Cas blushes at that, and he smiles down into his drink. “That’s a nice reminder,” he says. 

Sam gives him the most reassuring smile he can muster before getting to his feet. “Listen, I’ll go call him, see what’s up, and — Christ, it’s about  _ time _ , Dean!”

Cas turns around in his seat to see Dean making a beeline toward them. His face is flushed, shoulders heaving from exertion, and he wraps his arms around Cas’ shoulders, planting a kiss on his cheek. “Happy birthday, Cas,” he says.

“What happened?” Sam demands for Cas, who stands awkwardly in Dean’s embrace, unsure of how to react.

“My set,” Dean says, gesturing for a drink from the bartender. “It kept getting bumped back, and I couldn’t just leave.” He turns to Cas.

Sam’s face clouds over at that. “It’s your boyfriend’s birthday, Dean.”

Dean takes a long swig of his beer and glares at Sam. “You think I don’t know that? Jesus Christ.” He looks at Cas. “I’ll make it up to you. I promise.”

Cas smiles tightly. “It’s okay,” he says, unsure of who he’s trying to convince more, Dean or himself. “We’ll have plenty of birthdays to celebrate.”

* * *

Thinking back on it now, Cas wonders if that’s when things had really started going downhill.

Dean always seems to find new people to hang out with after his shows, and even though he does start performing earlier, just like he’d promised, Cas finds himself seeing him less and less. When he gets out of work, Dean’s just getting ready to head out. Sometimes they can squeeze in a quick dinner together, but more often than not, Dean’s already buzzed and distracted by nerves from upcoming shows.

Instead of talking about, well, anything, Cas finds himself acting as a soundboard for Dean’s bits, helping him craft the perfect joke or telling him when something falls flat or sounds awkward. He misses their old conversations about TV and food and the dirty sign language they’d been learning. It gets harder every time, but Cas keeps convincing himself that they’ll work through this.

They have to.

  
  


After spending four straight weekends switching between seasons of  _ Project Runway _ and  _ Cutthroat Kitchen _ , Cas can’t reply fast enough when he gets a text from Anna asking if he’d like to grab a drink and catch up.

“So,” she says soon after the waiter brings over their drinks, “how are things with Dean?”

Cas takes a long sip of his beer, and Anna smiles humorlessly.

“Guess that answers that.”

Cas swallows, then waves his hand dismissively. “It’s not that bad,” he amends. “It’s wonderful when we’re able to be together, but ever since  _ Harvelle _ —”

“He was great on it, by the way,” Anna interrupts, her smile warm this time.

Cas smiles back. “I’ll tell him you thought so. I’m so proud of him.” He clears his throat, then gets back on track. “Ever since  _ Harvelle _ , he’s been busier than ever. I know it’s important to him, and it’ll pay off in the long run, but it’s just…” He trails off and looks up at his sister. “I miss him.”

“You’re allowed to miss your boyfriend.” Anna purses her lips. “I don’t know if I’d be able to deal with it. And, I mean, I’d like to meet my brother’s boyfriend through something other than a late night TV show.”

Cas takes a deep breath, traces the cardboard coaster with his finger. He agrees with her, but can’t make himself verbalize it. “Honestly,” he finally says slowly, “I’d appreciate if we didn’t talk about it.”

“Sure.” Anna leans back a little and shakes her head. “Of course.” She takes a long sip of her drink, then continues, “ Claire’s tournament is in a couple weeks. Can you still go?”

Cas traces the rim of his glass with his finger and nods, but doesn’t look at his sister. “I hope you know what you’re doing with that,” he says. The idea of his niece participating in something as rough as roller derby is something that’s taken him more than a few months to get used to, and if he’s being honest, he’s still not completely comfortable with it.

Anna, however, waves his concerns away with a flick of her wrist. “You know she’s tough. She practices, she’ll be fine. Besides — ” she finishes off the rest of her drink before setting her empty glass back down on the table and grinning at Cas, “ — broken bones can heal, but memories last a lifetime.”

Cas blanches at that, any semblance of an appetite he’d had evaporating in an instant. “Not helping.”

His sister laughs. “I haven’t seen her this excited for something in a long time,” she says, and Cas softens. As much as he hates to admit it, Claire and roller derby are a match made in heaven.

“I’ll be there,” he says, mirroring the smile Anna gives him. 

“Perfect.” She rests her palms on the table and eases herself off of the tall barstool. “Bathroom run. Be right back.”

Cas nods and brings his glass back up to his lips, using the few minutes of solitude to take in the scene surrounding him. The restaurant is crowded with patrons: a few families, some solo diners, but the overwhelming majority are couples.

When he locks eyes on a couple splitting a plate of mozzarella sticks a few tables away, he feels a sudden yearning deep in his gut. He loves his sister, he really does, but he wishes he was waiting for Dean to get back from the bathroom instead.

Sitting in the middle of a sea of couples has made him realize just how fucking  _ weird _ their relationship is. It’s a Friday night, he should be out with his boyfriend, but instead, he’s with his sister and his boyfriend’s handing out flyers on street corners in Jackson Heights in exchange for three minutes in front of just as many people.

Cas downs the rest of his drink.

_ They met years ago at a theatre camp,  _ Cas thinks, resting his chin in one hand and observing the two young men.  _ They were good friends, spent all their time together at camp each summer, but eventually grew apart once middle school started. They didn't see each other for years until one day, they both won lottery tickets to  _ Dear Evan Hansen.  _ They sat next to each other, cried at the same moments, and grabbed drinks after the show. That led to exchanging numbers, a few dates, and here they are, four months later. _

Cas wonders if he comes across as having an interesting story to strangers, or if he's nothing but  _ Awkward dude in his early thirties has dinner with sister who takes pity on him because he's a loser with no friends. _

He shakes his head to rid himself of the thought and looks up to see Anna taking her place back at the table. She looks apologetic, and Cas purses his lips.

“What?”

“Claire's, uh, the babysitter needs a hand — ”

Cas doesn't need to hear anything else; he'll take any excuse he can to get away from his couples-laden thoughts. He pulls a twenty out of his wallet, smacks it down on the table, and grabs his jacket.

“Let's go.”

The door to Dean’s tiny studio apartment is unlocked when Cas tries the knob a few hours after his dinner with Anna, and he uses his shoulder to push it open with a sigh. When he enters, Dean is sitting on the couch, head hanging over the edge and legs draped over the back, staring at the TV.

He glances up when Cas enters and waves. “Hey,” he says, contorting himself so that he’s seated in a normal position before patting the spot next to him.

“You should really keep your door locked,” Cas says, sliding in next to Dean and resting his head on his shoulder. Dean’s arm automatically wraps around him, and he drops a quick kiss on his temple.

Dean barks out a laugh. “You think anyone’s gonna try to break into a place above a tattoo shop?” he asks, tapping his foot against the floor in time with the faint buzzing of needles that’s still audible through the wood.

“I don’t want you to get hurt,” Cas says, reaching up and tracing his finger gently along Dean’s cheekbone, where his bruise was the night they first met.

“Thanks, Mom, but I’ve got it covered.” His voice is affectionate, and Cas burrows deeper against his side. “How was tonight?

“It’s one in the morning. Not tonight anymore.”

Dean rolls his eyes. “Fine, how was last night?”

Cas shrugs. “Fine. Anna says hello. She still wants to meet you.”

“Set up a time.”

“That’s difficult to do when every single one of your nights is booked until two in the morning for the foreseeable future.” Cas can feel Dean stiffen slightly at that, but he doesn’t apologize.

An awkward silence grows between them, getting thicker by the second, until Dean sighs. “Listen, Cas, I know it sucks, but I promise — ”

“What are you doing on the 22nd?” Cas asks suddenly, shooting up and looking at Dean, eyes shining.

Dean hesitates. “That’s like, two weeks from now.”

“My niece, Claire, is competing in her first roller derby tournament,” Cas says. “It’s on a Saturday afternoon, so you won’t have to miss a set, and Anna will be there. You can meet them both.” He doesn’t want to look too hopeful when he and Dean make eye contact once more, but the opportunity is too perfect to pass up. 

Dean blinks owlishly, then flashes Cas a lazy grin. “Yeah. Let’s do it.” 

“Really?”

“‘Course.” For added emphasis, Dean digs his phone out of his pocket and types the event into his calendar. “I wanna meet your family. Or at least the ones you want me to meet.”

Cas cranes his neck up and kisses Dean, running his fingers along the close-cropped hair on Dean’s neck. “Thank you.”

Dean chuckles and pulls Cas closer, tangling their legs together on the coffee table. Cas keeps one hand resting on Dean’s neck, the other on his stomach, and closes his eyes. He eventually falls asleep to the steady rise and fall of Dean’s chest, punctuated by laugh tracks.


	8. Chapter 8

Cas isn’t sure if he’s more panicked or angry when Dean doesn’t answer his phone for the fourth time.

_ Hey, it’s Dean. You know what to do. _

Cas sighs and looks up toward the overcast sky while waiting for Dean’s voicemail to connect. “Dean, where are you? Claire’s race starts in ten minutes. Call me.” 

He had told Dean about Claire’s roller derby tournament weeks ago; he’d even put it into the calendar in his phone. Hell, he’d reminded him about it  _ two days ago _ , and still, he’s nowhere to be found. He turns off his phone and shoves it into his pocket before pulling his jacket up against the cold and heading back into the rink.

 

“Any luck?” Anna asks once Cas has stumbled back up the bleachers and taken his seat. 

He shakes his head, and feels Anna shift closer, wrapping her arm around him and squeezing his shoulder reassuringly. “I’m sure he’s fine, Cas,” she says. “Don’t worry.”

The rink’s ice has been temporarily replaced with sleek, polished wood, and the entire arena is buzzing with activity as both teams prepare for the upcoming competition. He searches for Claire’s helmet among the throngs of skaters, finally catching a glimpse of her blonde hair pulled into pigtails underneath her dark helmet.

Cas had been hesitant when Anna had told him that his only niece had taken an interest in roller derby, and downright terrified when Claire had shown up at his apartment one day to show him her new gear and tell him that she’d officially signed up to join the Gotham Girls Junior Derby League. 

“Nothing’s completely safe, Cas,” Anna had said, rubbing her brother’s back reassuringly as they watched Claire adjust her new helmet and secure her wrist guards. “Precautions are taken, and she’ll be learning the basics before she does anything involving contact. Don’t think I haven’t checked this out forward and backward.”

Cas hadn’t felt any better about the idea of Claire hip-checking other young girls into boards while getting hip-checked herself, but he’d been intrigued when she had come to him asking her to help with her derby name.

“What’s wrong with Claire?”

“It has to be rough,” Claire had said, as if explaining the most obvious thing in the world. “So people know not to mess with me.”

After getting further clarification from Anna—”Nothing  _ too _ rough or vulgar, please”—Cas and Claire had spent the afternoon brainstorming names. Claire Pains, Grace Clobber, and Pit of Desclaire came close, but when Cas had seen the way Claire’s eyes lit up at Triple Dog Claire You, he’d known that was the one.

Now, seeing the four words emblazoned on the back of Claire’s jersey fills Cas with an odd sense of pride. He can feel Anna’s eyes on him as he sets the small bouquet of flowers he’d picked up on the way over down next to him, and glances at her.

“Can I help you?”

She grins teasingly. “It’s not a dance recital, Cas.”

Cas raises his eyebrows in faux shock. “You don’t say.”

Anna shakes her head fondly before turning her attention back to the rink, where the competition is about to start. 

“You’re sure she’s ready for this?” Cas asks.

Anna smiles without turning back to him. “Don’t have much of a choice now,” she says. Cas looks down and notices the way she’s wringing her hands together nervously, and rests his hand on her arm. “She’ll be okay,” she says, sounding like she’s trying to convince herself of the fact just as much as Cas.

Claire, as it turns out, is more than okay. She’s in her element while she skates, dodging and slamming and hopping with the best of them, and Cas feels a surprising amount of pride as he watches her elbow the other girls. He and Anna yell and cheer and he hasn’t felt this good, this connected, in a long time.

He missed it.

 

After the competition is over, Anna and Cas meet Claire on the edge of the rink. 

“You did amazing, sweetie!” Anna says, scooping Claire up in a hug before she can protest. Cas hands her the rose when she’s free, and Claire rolls her eyes, but smiles anyway. “Is Dean here?” she asks, tucking her helmet under her arm and swiping strands of hair out of her eyes. 

Cas clears his throat and shakes his head. He had been so excited to introduce Dean to two of the most important people in his family, and the fact that he’s just disappeared makes a sour taste reappear in his mouth. “He’s sick,” he says, “but he told me to tell you to kick ass. He’ll be at the next one.”

Claire smirks at that while Cas tries not to be unsettled at how easily the lie comes.

 

Dean’s apartment is dark when Cas arrives. He palms around on the wall for the light switch, flicking it on and squinting into the tiny living room. The coffee table is littered with empty beer bottles and an ashtray with a still-smoldering cigarette resting inside; Cas stubs it out before heading toward Dean’s bed in the corner. 

Dean is sprawled out on his stomach, legs tangled in his blankets and sheets, his cheek pressed up against the pillow, a small puddle of drool pooling at his mouth. Cas closes his eyes and takes a breath, trying to stay calm, especially after catching sight of Dean’s phone, which is a few feet away, apparently tossed aside.

“Dean,” he says, keeping his voice neutral. “Dean, wake up.” He shakes his boyfriend’s arm for a few seconds and is met with a groan as Dean shifts positions, turning his head so that he’s not facing Cas anymore.

“Dean!” 

“Jesus, Cas,  _ what _ ?” Dean snaps.

“You told me you’d be at Claire’s competition today. It was two hours ago.”

Dean groans again and rolls over to face the wall, away from Cas. “Something came up.”

“That’s not—”

“I had a  _ set _ , Cas!” Dean says, his voice getting steadily louder. He stumbles to his feet, heads for the fridge, flings the door open, and starts rummaging around. Cas stares daggers into Dean’s back, and he stomps forward and slams the fridge door shut, almost catching Dean’s arm as he does so. 

Dean spins on his heel and glares at him, hugging his arm to his chest. “What the fuck was that?”

“I told you about Claire’s competition  _ weeks ago _ ,” Cas says, his voice low as he tries to keep himself composed. “It’s been on the calendar. I texted you about it on Tuesday.  _ Two days ago _ , Dean, and you told me then that you’d be there.”

“I got bumped up to opening a matinee show at Caroline’s, I couldn’t just—”

“You promised me.”

“Claire’ll have other competitions,” Dean finally snaps. “I needed to do this. I had to, it’s fucking  _ Caroline’s _ . I can go see Claire any time.”

Cas’ jaw locks in place, and he watches the way Dean’s face goes from defiant to hesitant at the motion.

“You can’t see her if we’re done, Dean,” Cas says quietly, and the color immediately drains from Dean’s cheeks. 

“Cas, I—”

“Do you even know how many things you’ve missed? Things you’ve half-assed?” Cas asks, defeated. “I spent my birthday talking to Sam more than you.”

“Sam’s a good guy—”

Dean’s voice is weak when Cas interrupts him with a sharp, “Sam’s not my  _ boyfriend _ .” He closes his eyes and takes a deep breath. “I know how happy comedy makes you, I know how much you love it. I know that, but I used to think you loved  _ me _ more.”

Dean grins, this time to hide his disbelief. “Cas, come on, you know you’re more imp—”

“That’s the whole point, Dean; I  _ don’t _ know. Everything you’ve done lately—or should I say ‘not done’—says the opposite. I don’t even know what to think anymore, and…” He pauses for a few seconds, trying to gather his thoughts. “I can’t do this anymore.”

Any remaining color in Dean’s face disappears as his jaw goes slack. His tongue darts out to wet his lips and Cas closes his eyes, trying to force the memories of those lips against his own out of his mind. He scoffs and looks down at the floor, shaking his head bewilderedly. “You really want to be the butt of all my jokes for the foreseeable future?”

“This isn’t a joke, Dean.”

Dean’s head shoots up at that, and he glares at him. “I thought you, you of all people, got me,” he says. “I thought you under _ stood _ —”

“You need to understand, too,” Cas snaps. “Comedy is  _ your _ life, not mine, and I’m sick of mine playing second fiddle. Tell me how many of my releases you’ve been to. How many times you’ve stayed up until two in the morning with me while I work out material—because it’s the same thing as being in a comedy club with you and five other people, Dean; it’s the same damn thing.”

Dean stares at him, and a few times, it looks like he’s about to say something; instead, he just shakes his head with a bewildered look on his face.

“Fuck you, Cas,” he finally says, and even though he’d been bracing himself for worse, this still stings more than Cas had been anticipating. They stand in silence for a few seconds and when Dean locks eyes with him, Cas has never seen him so serious. “Get the fuck out of here.”

“Dean—”

Dean stares at him and holds up two fingers in a peace sign. Cas tilts his head curiously, wondering if this is somehow Dean’s version of raising a white flag, when his index finger drops down, leaving Cas facing nothing but his middle finger.

“Fuck. Outta. Here.”

* * *

 

Cas turns his phone off when he changes his relationship status.

The last thing he wants to deal with is the questions and sympathies that secretly just want to know more about what happened. Instead, he writes. He takes all of the frustration and anger and sadness and fear and channels it into his laptop, writing for hours on end. He’s not entirely sure if it’s  _ good _ writing, but it’s progress, more than he had before, and Cas is proud of it.

He’s also proud of the fact that he checks Dean’s Instagram and Twitter once a day, as opposed to the once-an-hour he had been doing only a few days earlier.

According to those once a day checks, though, it doesn’t seem like their breakup did much when it came to dampening Dean’s spirits—if anything, he’s doing even  _ better _ . He’s spending more and more time out in Los Angeles, is constantly posting photos of himself with bigger and better comics, his follower counts jump by the hundreds, he gets thousands of likes within moments of posting—not that Cas has notifications set up to alert him to Dean’s posts or anything—and eventually, Cas has to hit the “block” button.

_ Just for now _ , he tells himself.  _ Just until I’m over it. Over him. _

All the free time Cas suddenly has turns into pages and pages of  _ One on One _ . Rewrites and outlines and shitty pages eventually turn into a rough draft, which gets passed on to Anna to review before it’s turned into a second, then a third.

When he starts to consider self-publishing as an option, Cas almost convinces himself that the book  _ isn’t _ done, that it’s not ready because a certain pair of bright green eyes hasn’t read it through yet.

_ He won’t _ , Cas tells himself.  _ This is as good as it’s going to get. _


	9. Chapter 9

Cas still hasn’t unblocked Dean a few weeks later when he’s heading home from work, a rough printer proof of his book in his messenger bag, and runs into a familiar face standing outside the Gramercy.

“Benny?”

Benny pulls his cigarette from his mouth and looks up; his eyes go bright in recognition. “Cas,” he says, blowing a thin line of smoke out of the side of his mouth before clasping Cas’ hand in his own. “How ya been, brother?”

“Could be better,” Cas answers. Benny seems thrown by his honesty; Cas is, too.

“I hear ya.” He glances around, then gives Cas a knowing, humorless grin. “Guess I can’t count on Dean bein’ here with you, huh?”

And there it is. “Uh, no,” Cas says, jamming his hands deeper into his jacket pockets. “I haven’t seen him in a while.”

“Well, that makes two of us.”

Cas’ eyebrows shoot up in surprise at that. “I thought you would’ve been in touch with him,” he says. “I was going to ask you how he was.”

Benny’s eyes dart down to his cigarette, a silent request for permission, and Cas nods. The man takes a long drag, tilts his head up, and blows smoke into the air slowly. “Haven’t heard from him in, hell, weeks, probably.”

“Really?”

“Mmhmm. Kid’s been hittin’ the pavement even more ever since he landed that spot on Harvelle, and he ain’t been showin’ up at the regular haunts. Outgrew us. Movin’ on up, I s’pose.”

Cas sighs deep, inhaling the remnants of Benny’s secondhand smoke as he thinks back to Dean attempting to justify missing Claire’s match to perform at Caroline’s, and he’s not surprised.

“‘S all payin’ off, though,” Benny continues, and Cas looks up sharply at him.

“What do you mean?”

He looks at Cas as if he just crawled out from under a rock. “Dean’s going on Crowley tonight.”

And Cas’ heart just about stops. Fergus Crowley, the number one name in late-night, the one Dean’s been trying so hard to impress. He wants to be thrilled, wants to cheer and celebrate, but getting the news from someone other than Dean himself almost immediately extinguishes the flicker of excitement he had had.

“Wow,” is all he can manage to say, and Benny chuckles.

“Damn right, wow,” he says. “Got it DVR’d and everything. Texted him that if he stops by the Gramercy again I’ll buy him a congratulatory meal. Haven’t heard anything back, though.”

“It’s tonight?” Cas asks, like he’s just come out of a haze.

Benny nods. “Don’t blame ya if you don’t want to watch, brother,” he says. “I wouldn’t, either, if I were in your shoes.”

“Yeah.” Cas sighs. “I think I have plans tonight anyway. Maybe I’ll catch the highlights later.” He looks up at Benny and extends his hand. “Good to see you, Benny.”

“You, too, brother. Stay good.”

* * *

 

Cas hears a familiar voice emanating through his apartment door as he pulls out his keys, and his heart seizes in his chest as he thinks for a split second that the voice might be the real thing. Searching for the right key to unlock the door, he pictures the warm, rough tone whispering in his ear and winces as his stomach twists up in knots.

_ It’s not him. He’s not here. He’s not coming back. _

When he opens the door, Balthazar is lounging on the couch, laptop resting on his chest. He cranes his neck to peer at Cas as he enters and waves absently. Dean’s voice from whatever standup set Balthazar is watching on YouTube permeates the apartment, and Cas wants to take a cold shower.

“Turn that off.”

“Have you seen it?”

“I don’t want to.”

“I think he misses you, Cassie.”

Cas rolls his eyes and sighs. “I’m not in the mood for jokes.”

His roommate shrugs. “For someone who used to date a comedian, you’ve sure got yourself a shitty sense of humor. Oh, that’s nice, thank you,” he says when Cas flips him off.

“I don’t want to hear him.”

Balthazar shakes his head. “Everyone’s talking about it,” he says, just as Dean swears and starts rambling in the video. “He’s upset, or something, and it’s bleeding through into his work. Something’s definitely on his mind, bothering him, and I think that  _ something’s _ got blue eyes and wears a trenchcoat in absurd weather conditions.”

Cas can’t help himself; he drops his messenger bag onto the kitchen table and looks over Balthazar’s shoulder. Dean is on stage at a club in California, based on the video’s caption, and instead of using his casual, storytelling style that made him so popular in the first place, his words are jilted, thoughts scattered. He’s almost jumpy, running a hand through his hair over and over as he walks the room. Even for the few seconds he watches, Cas is reminded of all the times he’d seen Dean drunk, and sighs.

He can’t watch it anymore.

“He’s going to be on Crowley tonight,” Cas says quietly, and Balthazar’s eyebrows shoot up.

“No shit?”

Cas shakes his head.

“You gonna watch?”

Cas purses his lips, considering it for a second, but finally shakes his head again. “No,” he says, heading for his room. “I think I’d like to turn in early.”

Balthazar barks out a laugh, closing out of the page playing Dean’s video. “Yeah, we’ll see how long that lasts.”

Cas rolls his eyes and closes the door behind him, determined to prove Balthazar wrong.

 

Two hours later, Cas is staring sullenly at the TV, watching Crowley interact with Max and Alicia Banes, a directing duo famous for their supernatural flicks. Dean must be in heaven right now; he loves Banes movies. Cas wonders why he’s even forcing himself through this. Nobody told him he had to watch Dean—hell, Benny and Balthazar practically just told him  _ not to _ —but he can’t help himself. 

_ Just to see how badly he bombs. _

Cas zones out during the interview and doesn’t notice the time until Crowley is in the middle of doing his sign-off. He off-handedly throws out an apology to Dean, that they ran out of time and they’ll have him back soon, wishes everyone a good night, and then the credits start to roll across the bottom of the screen.

Cas’s heart clenches in his chest, and he turns the TV on mute.

Well, then.

He sits in silence for a few seconds, sipping on his beer, before scrubbing a hand down over his mouth, a goddamn tic he picked up from Dean. He wonders what’s happening out in LA right now, if Dean’s all right, if he has anyone out there to make sure he doesn’t do anything stupid. Cas hasn’t been to a single comedy club since they broke up, and he starts to wonder once again if Dean’s found someone else. Someone who could support him the way Cas couldn’t, who was willing to forsake anniversary plans for shows, who was just... _ better  _ than him.

Before he can think about it anymore, he dials Dean’s number, puts the phone on speaker, and waits.

His stomach flips with every ring as he struggles to decide whether he wants Dean to answer.

The call goes to Dean’s voicemail, and once again, Dean’s made the decision for him.

He doesn’t leave a message, instead typing out a quick, two-word text.

_ Cas, 12:02am: I’m sorry. _

* * *

 

Cas is looking for some background info for his latest piece when he stumbles upon the article.

_ Winchester Spirals Following Crowley Snub _

_ Has comedy’s newest golden boy already fizzled out? _

_ After what appeared to be a legendary career in the making, up-and-coming local boy Dean Winchester has experienced some of the first roadblocks in his young career. His set on  _ Late Night with Jo Harvelle _ had been everything audiences want from a comic: quick, witty, and most importantly, funny. His casual style of unraveling jokes through longform storytelling makes fans feel as though it’s just them and Winchester, grabbing a drink at the bar as he regales them with tales about his life and family that are simultaneously heartbreaking, hysterical, and in some cases, unbelievable. He’s genuine, sharp, and unlike anything the comedy scene had seen in years. _

_ That openness undoubtedly played a large part in him landing a spot on  _ The Tonight Show  _ to begin with, but once his spot was bumped this past Friday night, it seems Winchester has gone into a bit of a tailspin. He’s closed himself off, been less forthcoming, and, in the process, has closed off access to the comedy stylings that launched him in the first place. _

_ He had everything going for him, and then, it all just...stopped. _

_ Frankly, it’s unclear whether or not Winchester’s ready for the spotlight, or if he’ll ever be able to earn a spot among the ranks of Linda Tran, Missouri Moseley, Victor Henriksen, and other comedy greats. _

_ If I had to guess, based on his recent intoxicated rants at open mics in both New York and Los Angeles, my answer would be a resounding no. _

Cas swallows hard, fighting to stop his eyes from clouding over with tears and the ruthlessness of the statements made against Dean. He shouldn’t care, he  _ knows _ he shouldn’t, but he’s not going to convince himself of that by continuing to stare at a computer screen for the rest of the afternoon.

After a quick survey of the office around him, he grabs his bag and sneaks out the back stairwell. No one would stop him if he left through the main entrance, but he’s just not in the mood to deal with most humans, even those as docile as Alfie, the office’s receptionist.

It’s a nice day, so Cas decides to take a walk through the city and before he knows it, ends up outside of the Strand. Because it’s a work day, the shop is a bit less crowded than usual, and Cas decides to take advantage. If he gets caught, he can just say he was stopping in to buy supplies.

He makes a beeline for the notebooks and starts flipping through them, deciding on a few that he’d like to bring home. He’s about to head for the register when a faded flannel shirt and scuffed workboots catch his eye.

“Dean.”

Dean looks up from where he’s reading the back cover of a new release. A tight smile is already plastered on his face, so Cas assumes he’d been expecting a fan. When he sees him, though, Dean’s eyes widen behind the lenses of his glasses, and he looks around, trying to find an escape route. Cas almost does the same thing, but instead, swallows hard and takes a few steps forward.

As Cas approaches, Dean fumbles for his glasses and shoves them into his back pocket. “Hi,” he says quickly. “Sorry, I’ll — ” Dean trails off, but gestures vaguely toward the exit, and starts to make his way there.

Cas sidesteps, stopping Dean in his tracks. “You can stay,” he says. “I don’t own the Strand.”

“Yeah, but you showed me this place.”

“I don’t own the Strand, Dean,” Cas repeats, his voice going softer this time. He’s not sure, but he thinks he catches the corners of Dean’s mouth twitch upwards; he blinks, though, and they’re back to normal.

Dean huffs out a self-conscious little laugh. “Been a while,” he says, resting a hand on a nearby stack of books and rubbing the back of his neck with the other.

Cas nods. “How are things?”

Dean shrugs one shoulder. “I, uh, I’m stayin’ with Sam and Eileen til things get a little more...situated.” His voice, his entire demeanor, is sheepish, and the absence of Dean’s regular confidence makes Cas uneasy.

Cas should pay for his notebooks and go back to work. He should wish Dean well, buy himself a cheap bottle of wine on the way home from the office, and pretend this whole encounter never happened.

He should  _ do _ all that, but that’s not what he  _ needs _ .

“Do you want to get some coffee?”

 

“I saw you on Crowley,” Cas says before almost immediately recognizing his gaffe. “I, I mean — ”

Dean laughs humorlessly and takes a sip of his coffee. “I know.” He stares down into his cup for a few seconds, then glances up quickly at Cas. “Uh, how you been?”

_ How have I been _ . 

Cas’ breath catches in his throat as a flurry of adjectives start running through his head.  _ Terrible. Angry. Depressed. Annoyed. Guilty. Remorseful. _

“All right,” he finally settles on. “Just working a lot. What about you?”

Dean shrugs a single shoulder and looks like he wishes there was something a little stronger than coffee in his cup. “Could be better,” he says quietly.

Cas doesn’t know what to say to that, if he should be prying or just let it be, but Dean makes that decision for him.

“Saw you have a book coming out,” Dean says uncertainly, quick to change the subject. “That’s cool.”

Cas shrugs. “Just a self-published thing. Not that cool.”

“Nah,” Dean says, shaking his head. “Very cool. Is it the same thing I saw a while ago? The same story, I mean?”

“Yes,” Cas says. “Edited to the point of being unrecognizable from what you saw, though.”

Dean grins. “Well, congrats.”

“Thank you.”

They sit in the awkward silence for a moment, and Cas feels like he’s drowning. He wants to be the one to break the silence, to ask Dean what he was thinking, why he put everything else on the backseat, why he didn’t fight more for Cas, and, against his better judgement, if he’d be willing to give things another try.

Dean beats him to it. “Hey, Cas?”

“Yes?”

Dean hesitates, then asks, “Why were you even watching?”

Cas blinks. He’d been trying to answer that same exact question himself for weeks now. “I don’t know,” he finally admits. “I think at first I just wanted to see you bomb — ” Dean chuckles humorlessly “ — but even with everything that happened, I know how important landing that spot was to you. How hard you worked for it. And I just, I don’t know, wanted to see it happen.”

“Yeah, me, too,” Dean mutters.

And Dean just looks so sad, so dejected and hopeless, that Cas reaches across the table without thinking and grabs his hand. Dean straightens immediately and stares at Cas, who pulls his hand away. “Sorry,” he falters. “Sorry, force of habit.” He clears his throat and glances down at his lap. “But it will happen, Dean.”

“Dunno about that.” 

“Dean — ”

“I fucked it up,” Dean interrupts. “Every single thing. I fucked over anyone who gave a shit about me, just to try to make strangers laugh for a few minutes with a joke they’d forget about the next goddamn day. I did what they say, about risking everything for what you love, and it wasn’t fucking worth it.”

Cas wants to argue with Dean, to tell him that he’s wrong, but in all honesty, he’s not. 

“I fucked you over,” Dean continues, “you deserved so much better than me, and I just...I know that.” He gets to his feet, and Cas can feel his heart starting to weigh himself down as he looks up at Dean, feeling like he’s staring up at him from the bottom of a well. “I’m not gonna waste any more of your time,” he continues. “I hope you find someone who treats you right, and I’m sorry it wasn’t me.”

He gives Cas one more half-hearted smile before heading for the exit.

“Dean,” Cas says. His heart jumps at the way Dean immediately stops in place and turns back around to face him. “I, uh, I’m having a reading tomorrow. For my book. At the Booksmith. At noon.” The simple words sound foreign in his mouth and he cringes internally at how choppy they sound coming out. 

Dean doesn’t say anything. He just looks at Cas, like he’s waiting for the punchline. When one doesn’t come, he looks down and walks out of the coffee shop.


	10. Chapter 10

_ He’s here on a dare, _ Cas thinks of the man sitting in the front row, flipping idly through his book.  _ Or he thinks I’m someone else. The second I start reading, he’ll realize I’m a hack and leave. He has a master’s in classic literature, and he’s bitter that his novel hasn’t gotten published yet. _

_ Stop it, Cas _ . He retreats from peeking through the crack in the door, cracks the bones in each of his fingers one by one, and looks down at his own tattered copy of his book. It’s his baby, one of the only things that’s been able to help him get his mind off anything else going on in his life, and the idea of its finality and the fact that anyone can now read it and judge him is terrifying.

The store’s manager, a slick, smooth-talking woman named Ruby, greets him in the back room. “Hi, Cas,” she says, grinning and offering her hand for a shake. “So good to meet you, this is so cool.” Her smile widens when she catches a glimpse of Cas’ book in his hand. “It was  _ so _ fucking good,” she adds. “I loved it.”

Even though the last thing he wants to do is smile, Cas can’t help the corners of his mouth tugging upward at Ruby’s enthusiasm. “Thank you.”

“You ready? We’ve got a full house out there.”

Cas raises an eyebrow, and Ruby quickly amends her statement. “I mean, the rare books room is pretty small, but you filled it; no lies here.” She spreads her hands wide and grins. “Congratulations.”

“Thank you,” Cas says again. He gets to his feet and smooths out his shirt before nodding at Ruby. “Ready.”

Ruby hadn’t been lying; the Booksmith’s rare books room is tiny — not much bigger than his and Balthazar’s living room — but almost all of the fifteen or so aluminum folding chairs are taken. Tepid applause (louder from Anna, Claire, and Gabe, who he spots right away in the front row) rings out from the audience when he enters, and he waves awkwardly.

Ruby makes a brief introduction of him and his book before letting him take her spot behind the podium. Cas smiles gratefully at her and grips his book tighter to try and prevent anyone from seeing his trembling hands. 

“I, thank you all for coming,” he says. “I know this is a small, little book, but it means…”

He trails off when his eyes lock with a familiar pair of green ones in the very last row. Dean has a few empty seats around him, as if he’s surrounded by some kind of forcefield, and Cas suddenly feels a lump in his throat. 

Dean flushes and the familiar crinkles around his eyes reappear when he realizes that Cas has spotted him. He gives him a hopeful little smile, and Cas swallows hard.

“It means a lot,” he says, not taking his eyes off Dean.

Cas holds eye contact with Dean for a few more seconds, and his cheeks go red when Dean winks at him. He smiles down at his hands, glances back up at Dean, then opens his book.


End file.
